Phenyl-substituted-2enamino-keto nitriles

ABSTRACT

The present invention relates to novel phenyl-substituted 2-enamino-ketonitriles of the formula (I):  
                 
 
     in which 
     Ar, X, Z, Y and K are each as defined in the description,  
     to a plurality of processes for their preparation and to their use as herbicides and pesticides.

[0001] The invention relates to novel phenyl-substituted2-enamino-ketonitriles, to a plurality of processes for theirpreparation and to their use as crop protection agents, in particular asherbicides, acaricides, nematicides and insecticides

[0002] Certain 2-enamino-ketonitriles which are substituted on thephenyl ring and have herbicidal action have already been disclosed, forexample in EP-A 0 348 002. However, these 2-[3-phenoxy- or3-[(2-pyridyloxy)benzoyl]-3-(dialkylamino)acrylo-nitriles have hithertonot attained any importance.

[0003] Likewise without any significant importance are the compoundswith herbicidal properties disclosed in JP-A2 10 175 937, WO 99/16753and EP-A 0 490 220.

[0004] Furthermore, 2-enamino-ketonitriles have been disclosed for useas intermediates for the synthesis of antibacterial active compounds,see DE-A 35 02 935, EP-A 0 220 523, DE 34 26 483 and EP-A 0 168 737.

[0005] Further 2-enamino-ketonitriles are also known from DE-A 19 958164, DE-A 19 851 986, DE-A 10 007 286 and WO 00/27812.

[0006] Also known are 2-enamino-ketonitriles which are unsubstituted onthe phenyl ring (I. N. Sobhy, H. S. Zahi, M. M. Hassan, E. M. Hilmy,(Chem. Ind. (London), 1988, 17, 563-564), I. N. Sobhy, M. M. Hassan, E.M. Hilmy (Arch. Pharm. 1987, 320 (6), 487-491), E. A. Ghani, M. A.Fathy, F. A. Amer, Collet. Czech, Chem. Commun. (1986, 51, 2193-2198),C. Degrand, G. Belot, P-L. Compagnon, F. Jasquez, Can. J. Chem. (1983,61, 2581-2589), E. M. Hilmy, M. S. Fahmy, E. A. A. Hafez, R. M.Elmoghayar J. Heterocyl. Chem. (1979, 16, 1109-1111), H. Schäfer, K.Gewald, Monatsh. Chem. (1978), 109, 527-535). M. Savkar, S.Chattopadhyay, K. K. Mahalanabis, Ind. J. Chem. Sect. B (1996, 25 B,1133-1137). Z. E. S. Kandeel, F. M. Abelrazeh, M. E. Eldin, J. Chem.Soc. Perk. Trans. 1 (1985, 7, 1499-1501), H. Jurek, H. W. Schmidt, G.Gfrerer, Synthesis, (1982, 9, 791) K. Gewald, H. Schafer, K. Sattler,Monatsh. Chem. (1979, 110, 1189).

[0007] However, a use of these compounds as crop protection agents hashitherto not been described.

[0008] The formula (I) provides a general definition of the novel2-enamino-ketonitriles

[0009] in which

[0010] K represents oxygen or sulphur,

[0011] Ar represents in each case optionally substituted phenyl,naphthyl, represents in each case optionally substituted mono- orbicyclic hetaryl having 5 to 10 ring atoms, or represents the group

[0012]  where

[0013] B¹ represents hydrogen or halogen,

[0014] two adjacent radicals—B² and B³ or B³ and B⁴—together representone of the groupings below

[0015] —Q¹—CQ²—, —Q¹—CQ²—Q³—, —Q¹—C(B⁶,B⁷)—Q³—, —C(B⁶,B⁷)—CQ²—,—C(B⁶,B⁷)—Q¹—CQ²—, —Q¹—C(B⁶,B⁷)—C(B⁶,B⁷)—, —Q¹—C(B⁶,B⁷)—C(B⁶,B⁷)—Q³—,—C(B⁶,B⁷)—C(B⁶,B⁷)—CQ²—, —Q¹C(B⁶)═C(B⁶)—, —C(B⁶)═C(B⁶)—CQ²—,—Q¹—C(B⁶,B⁷)—CQ²—, —N(B⁸)—C(B⁶,B⁷)—CQ²—, —C(B⁶)═N—, —Q¹—CQ²—C(B⁶,B⁷)—,—Q¹—CQ²—N(B⁸)—, —Q¹—C(B⁶,B⁷)—CQ²—N(B⁸)—, —C(B⁶,B⁷)—Q¹—CQ²—N(B⁸)—,—C(B⁶,B⁷)—C(B⁶,B⁷)—N(B⁸)—, —C(B⁶,B⁷)—C(B⁶,B⁷)—CQ²—N(B⁸)—,—C(B⁶)═C(B⁶)—N(B⁸)—, —C(B⁶)═C(B⁶)—CQ²—N(B⁸)—, —C(B⁶B⁷)—CQ²—N(B⁸)—N(B⁸)—C(B⁶,B⁷)—CQ²—N(B⁸)—, —C(B⁶)═N—N(B⁸)—, —Q¹—CQ²—C(B⁶,B⁷)—N(B⁸)—,—Q¹—C(B⁶,B⁷)—C(B⁶,B⁷)—CQ²—N(B⁸)—, —N(B⁸)—CQ²—C(B⁶)═N—,—Q¹—C(B⁶)═C(B⁶)—Q³—, —N(B⁸)—C(B⁶)═C(B⁶)—CQ²—, —N(B⁸)—C(B⁶)═N—,—N(B⁸)—C(B⁶,B⁷)—C(B⁶,B⁷)—Q³—, —N(B⁸)—CQ²—C(B⁶,B⁷)—Q⁴—,—N(B⁸)—CQ²—CQ²—Q³—, —Q¹—C(B⁶)═C(B⁶)—C(B⁶,B⁷)—, —Q¹—C(B⁶)═C(B⁶)—,

[0016] and the fourth radical, B⁴ or B², represents hydrogen,thiocarbamoyl, cyano or halogen,

[0017] where

[0018] Q¹, Q² and Q³ are identical or different and each representoxygen or sulphur, and

[0019] Q⁴ represents —SO— or —SO₂—,

[0020] B⁶ and B⁷ are identical or different and individually representhydrogen, halogen or alkyl or together represent alkanediyl, and

[0021] B⁸ represents hydrogen, hydroxyl, represents in each caseoptionally cyano-, halogen-, alkoxy-, alkylcarbonyl- oralkoxycarbonyl-substituted alkyl, alkylcarbonyl, alkoxycarbonyl,alkylthio or alkylsulphonyl, represents in each case optionallyhalogen-substituted alkenyl or alkinyl, represents in each caseoptionally halogen- or alkyl-substituted cycloalkyl or cycloalkylalkyl,represents in each case optionally halogen-substituted alkoxy oralkenyloxy, represents in each case optionally cyano-, halogen-, alkyl-,halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyl orarylalkoxy,

[0022] X represents CN,

[0023] Y represents hydrogen, represents in each case optionallysubstituted alkyl, alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl,represents in each case optionally substituted cycloalkyl orcycloalkylalkyl which are in each case optionally interrupted in thecycle by heteroatoms, or represents in each case optionally substitutedphenylalkyl or hetarylalkyl,

[0024] Z represents hydrogen, represents in each case optionallysubstituted alkyl, phenyl or phenylalkyl,

[0025] R¹ represents hydrogen, represents in each case optionallysubstituted saturated or unsaturated alkyl or cycloalkyl, each of whichis optionally interrupted by heteroatoms, represents in each caseoptionally substituted phenyl or hetaryl, represents in each caseoptionally substituted phenylalkyl or hetarylalkyl, and

[0026] R² represents hydrogen, represents in each case optionallysubstituted saturated or unsaturated alkyl or alkoxy, represents in eachcase optionally substituted phenyl, phenylalkyl or phenylalkyloxy, or

[0027] R¹, R² furthermore together with the nitrogen atom to which theyare attached represent an optionally substituted cycle which isoptionally substituted by a plurality of heteroatoms.

[0028] For the compounds of the formula (I), the following applies:

[0029] Ar preferably represents Ar¹, where Ar¹ represents phenyl,naphthyl or mono- or bicyclic hetaryl having five to ten ring atoms,each of which radicals is optionally mono- to pentasubstituted byhalogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkinyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-alkinyloxy, C₁-C₈-alkyl-thio,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkyl, C₁-C₆-halogenoalkoxy,C₂-C₈-halogenoalkenyloxy, C₁-C₂-alkylidenediyl-dioxy,C₁-C₂-halogenoalkyli-denediyl-dioxy, halogeno-C₁-C₄-alkylthio,halogeno-C₁-C₄-alkylsulphonyl, phenyl-C₁-C₄-alkoxy, hydroxyl, mercapto,nitro, cyano, amino or by the groups

[0030]  or represents Ar², where Ar² represents Ar¹ which isadditionally substituted by phenyl, naphthyl, five- or six-memberedhetaryl, phenyl-C₁-C₄-alkyl, phenoxy, phenyl-S(O)_(g)-, five- orsix-membered hetaryloxy or hetaryl-S(O)_(g), where these substituentsfor their part are in each case optionally mono- to tetrasubstituted byhalogen, C₁-C₆-alkyl, C₁-C₆-alkenyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, nitro or cyano, where g represents 0, 1 or 2,

[0031] or represents the group

[0032] where

[0033] B¹ represents hydrogen or halogen,

[0034] two adjacent radicals—B² and B³ or B³ and B⁴—together representone of the groupings below

[0035] —Q¹—CQ²—C(B⁸)—, —Q¹—C(B⁶,B⁷)—CQ²—N(B⁸)—,—N(B⁸)—C(B⁶,B⁷)CQ²—N(B⁸)—, —Q¹CQ²—C(B⁶,B⁷)—N(B⁸)—,—Q¹-C(B⁶)═C(B⁶)—C(B⁶,B⁷)—, —Q¹—C(B⁶)═C(B⁶)—, —N(B⁸)—CQ²—C(B⁶)═N—

[0036] where

[0037] Q¹ and Q² are identical or different and each represent oxygen orsulphur,

[0038] B⁶ and B⁷ are identical or different and individually representhydrogen or methyl,

[0039] B⁸ represents hydrogen, hydroxyl, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, acetyl-,propionyl-, methoxycarbonyl- or ethoxycarbonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each caseoptionally fluorine-, chlorine- or bromine-substituted propenyl,butenyl, propinyl or butinyl, represents in each case optionallyfluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, represents ineach case optionally fluorine- and/or chlorine-substituted methoxy,ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy,or represents in each case optionally cyano-, fluorine-, chlorine-,methyl-, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy-or trifluoro-methoxy-substituted benzyl or benzyloxy,

[0040] and the fourth radical, B⁴ or B², represents hydrogen, cyano,fluorine or chlorine,

[0041] K preferably represents oxygen or sulphur.

[0042] L preferably represents oxygen or sulphur.

[0043] X preferably represents CN

[0044] Y preferably represents hydrogen, in each case optionally mono-or poly-hydroxy-substituted C₁-C₁₂-alkyl, C₃-C₁₀-alkenyl,C₃-C₁₀-alkinyl, C₁-C₆-alkoxy-C₂-C₄-alkyl, di-C₁-C₆-alkoxy-C₂-C₄-alkyl,C₁-C₆-alkoxy-C₂-C₄-cyanoalkyl, C₁-C₆-alkylthio-C₂-C₄-alkyl,C₁-C₈-halogenoalkyl, C₁-C₈-halo-genoalkenyl or C₁-C₈-cyanoalkyl,represents in each case optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, cyano-, halogenophenyl-, benzyl-,C₁-C₆-hydroxyalkyl- or halogen-substituted C₃-C₈-cycloalkyl orC₃-C₈-cycloalkyl-C₁-C₄-alkyl which are optionally interrupted in thecycle by oxygen, sulphur or nitrogen, represents phenyl-C₁-C₄-alkyl orfive- or six-membered hetaryl-C₁-C₄-alkyl, each of which is optionallymono- to tetra-substituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

[0045] Z preferably represents hydrogen, C₁-C₆-alkyl, represents phenylor phenyl-C₁-C₄-alkyl, each of which is optionally mono- totrisubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano.

[0046] R¹ preferably represents hydrogen, represents in each caseoptionally fluorine-and/or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₁₀-alkenyl, C₃-C₆-alkinyl, represents in each case optionallyfluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-substitutedC₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which optionally one methylenegroup may be replaced by oxygen or sulphur, or represents phenyl,pyridyl, thienyl, pyrimidyl, thiazolyl, phenyl-C₁-C₄-alkyl,pyridyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each of which is optionallymono- to tetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

[0047] R² preferably represents hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl.

[0048] R¹, R² preferably furthermore together with the nitrogen atom towhich they are attached represent an in each case optionallyC₁-C₄-alkyl-substituted five- to eight-membered cycle in whichoptionally one methylene group may be replaced by oxygen or sulphur.

[0049] R³ preferably represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkinyl,C₁-C₁₀-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, ineach case optionally fluorine-, chlorine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenoxy, benzyloxy, five- or six-membered hetaryl orphenyl-C₁-C₄-alkyl, each of which may optionally be mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, or, in thecase of the radicals a), c) and f) mentioned under Ar, also represents agroup

[0050] R⁴ preferably represents hydrogen or C₁-C₄-alkyl.

[0051] R⁵ preferably represents hydrogen or optionally fluorine- and/orchlorine-substituted C₁-C₄-alkyl.

[0052] R⁶ preferably represents hydrogen, in each case optionallyfluorine- and/or chlorine-substituted C₁-C₁₀-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy, C₃-C₈-alkenyloxy, optionally fluorine-,chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one methylene group may be replaced by oxygen orsulphur, represents phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₂-alkoxy,each of which may optionally be mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro.

[0053] R⁷ preferably represents hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl.

[0054] R⁶, R⁷ preferably furthermore together with the nitrogen atom towhich they are attached represent an optionally C₁-C₄-alkyl-substitutedfive- to eight-membered cycle in which optionally one methylene groupmay be replaced by oxygen or sulphur.

[0055] K particularly preferably represents oxygen or sulphur.

[0056] Ar particularly preferably represents Ar¹, where Ar¹ representsphenyl, naphthyl, quinolinyl, thienyl, pyrimidyl, furanyl, thiazolyl,benzothiazolyl, oxazolyl, pyrazolyl or pyridyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₁-C₆-alkylthio,C₁-C₄-alkyl-sulphonyl, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,C₂-C₄-halogeno-alkenyloxy, C₁-C₂-alkylidenediyl-dioxy,C₁-C₂-halogenoalkylidenediyl-di-oxy, halogeno-C₁-C₂-alkylthio,halogeno-C₁-C₂-alkylsulphonyl, phenyl-C₁-C₄-alkoxy, hydroxyl, mercapto,nitro, cyano, amino or by one of the groups below

[0057] or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, pyrimidyl, thienyl, furanyl, thiazolyl,tetrazolyl, triazolyl, benzyl, phenoxy, phenyl-S(O)_(g)—, pyridyloxy,pyrimidyloxy, thiazolyloxy, pyridyl-S(O)_(g)—, pyrimidyl-S(O)_(g)— orthiazolyl-S(O)_(g)—, where these substituents for their part areoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₂-C₄-alkenyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, where g represents 0, 1 or 2,

[0058] or represents the group

[0059]  where

[0060] B¹ represents hydrogen or halogen,

[0061] two adjacent radicals—B² and B³ or B³ and B⁴—together representthe grouping below

—Q¹—C(B⁶,B⁷)—CQ²—N(B⁸)—,

[0062]  where

[0063] Q¹ and Q² are identical or different and each represents oxygenor sulphur,

[0064] B⁶ and B⁷ are identical or different and individually representhydrogen or methyl,

[0065] B⁸ represents hydrogen, hydroxyl, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, acetyl-,propionyl-, methoxycarbonyl- or ethoxycarbonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each caseoptionally fluorine-, chlorine- or bromine-substituted propenyl,butenyl, propinyl or butinyl, represents in each case optionallyfluorine-, chlorine-, bromine-, methyl- or ethyl-substitutedcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, represents ineach case optionally fluorine- and/or chlorine-substituted methoxy,ethoxy, n- or i-propoxy, n-, i- or s-but-oxy, propenyloxy or butenyloxy,or represents in each case optionally cyano-, fluorine-, chlorine-,methyl, ethyl-, trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted benzyl or benzyloxy,

[0066] and the fourth radical, B⁴ or B², represents hydrogen, cyano,fluorine or chlorine,

[0067] X particularly preferably represents CN,

[0068] Y particularly preferably represents hydrogen, represents in eachcase optionally mono- or poly-hydroxy-substituted C₁-C₁₀-alkyl,C₁-C₆-halogenoalkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₄-alkoxy-C₂-C₃-alkyl, di-C₁-C₄-alkoxy-C₂-C₄-alkyl,C₁-C₄-alkoxy-C₂-C₄-cyanoalkyl, C₁-C₄-alkylthio-C₂-C₃-alkyl,C₁-C₆-halogenoalkenyl or C₁-C₆-cyanoalkyl, represents in each caseoptionally C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-, cyano-,halogenophenyl-, benzyl-, C₁-C₄-hydroxyalkyl-. fluorine- orchlorine-substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₂-alkyl inwhich optionally one methylene group may be replaced by oxygen ornitrogen, represents phenyl-C₁-C₃-alkyl, thiazolylmethyl,triazolylmethyl or pyridylmethyl, each of which is optionally mono- totrisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro.

[0069] Z particularly preferably represents hydrogen, C₁-C₃-alkyl,represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro or cyano.

[0070] R¹ particularly preferably represents hydrogen, represents ineach case optionally fluorine and/or chlorine-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl, C₃-C₄-alkinyl, represents optionally fluorine-,chlorine-, C₁-C₂-alkyl-, C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl orrepresents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro.

[0071] R² particularly preferably represents hydrogen, representsC₁-C₄-alkyl or C₃-C₄-alkenyl, each of which is optionally substituted byfluorine and/or chlorine.

[0072] R¹,R² particularly preferably furthermore together with thenitrogen atom to which they are attached represent an optionallymethyl-substituted five- or six-membered cycle in which optionally onemethylene group may be replaced by oxygen,

[0073] R³ particularly preferably represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, in each case optionally fluorine-,chlorine-, C₁-C₂-alkyl- and/or C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkylor C₃-C₆-cycloalkoxy in which optionally one methylene group may bereplaced by oxygen, represents phenyl, phenoxy, benzyloxy, thienyl,furanyl, pyridyl, pyrimidyl, thiazolyl, pyrazolyl or phenyl-C₁-C₂-alkyl,each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, cyano or nitro, or, in the case ofthe radicals a), c) and f) mentioned under Ar, also represents a group

[0074] R⁴ particularly preferably represents hydrogen.

[0075] R⁵ particularly preferably represents hydrogen, methyl or ethyl.

[0076] R⁶ particularly preferably represents hydrogen, in each caseoptionally fluorine-and/or chlorine-substituted C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, in whichoptionally one methylene group may be replaced by oxygen, representsphenyl or phenyl-C₁-C₂-alkyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro.

[0077] R⁷ particularly preferably represents hydrogen or C₁-C₄-alkyl.

[0078] R⁶, R⁷ particularly preferably furthermore together with thenitrogen atom to which they are attached represent an optionallyC₁-C₂-alkyl-substituted five- or six-membered cycle in which optionallyone methylene group may be replaced by oxygen.

[0079] K very particularly preferably represents oxygen and sulphur.

[0080] Ar very particularly preferably represents Ar¹, where Ar¹represents phenyl which is optionally mono- to trisubstituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i-or t-butyl, methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy,allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy,methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy,methylenedioxy, difluoromethylenedioxy, tetra-fluoroethylenedioxy,difluoromethylthio, trifluoromethylthio, trifluoromethyl-sulphinyl,trifluoromethylsulphonyl, benzyloxy, hydroxyl, mercapto, nitro, cyano oramino, or represents pyridyl which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, propoxy,i-propoxy, butoxy, i-butoxy, methylthio, ethylthio or trifluoromethyl,

[0081] or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl orphenoxy, where these substituents are for their part optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- ort-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano,

[0082] or represents the group

[0083]  where B¹ represents hydrogen or fluorine and B⁸ representsallyl, propargyl or benzyl,

[0084] X very particularly preferably represents —CN, —CO—NH₂,

[0085] Y very particularly preferably represents hydrogen, in each caseoptionally mono- or poly-hydroxy-substituted C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl,C₁-C₄-alkoxy-C₂-C₃-alkyl, di-C₁-C₂-alkoxy-C₂-C₄-alkyl,C₁-C₂-alkoxy-C₂-C₄-cyanoalkyl, C₁-C₂-alkylthio-C₂-C₃-alkyl,C₁-C₅-halogenoalkenyl or C₁-C₆-cyanoalkyl, represents in each caseoptionally methyl-, methoxy-, ethoxy-, trifluoromethyl-, cyano-,chlorophenyl-, benzyl-, hydroxymethyl-, fluorine- orchlorine-substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₂-alkyl inwhich optionally one methylene group may be replaced by oxygen orsulphur, represents benzyl, phenethyl or pyridylmethyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy,cyano or nitro.

[0086] Z very particularly preferably represents hydrogen, methyl,ethyl, represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, trifluoro-methoxy, cyano or nitro.

[0087] R³ very particularly preferably represents methyl, ethyl, propyl,isopropyl, n-, s-, i- or t-butyl, vinyl, trifluoromethyl, methoxy,ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butyloxy, cyclopropyl,cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, representsphenyl, pyridyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, n-, s-, i- ort-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, orin the case of the radicals a), c) and f) mentioned Ar, also representsthe group

[0088] R⁵ very particularly preferably represents hydrogen or methyl.

[0089] R⁶ very particularly preferably represents hydrogen, methyl,ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl,cyclopentyl, cyclohexyl, represents phenyl which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro

[0090] R⁷ very particularly preferably represents hydrogen, methyl orethyl.

[0091] R⁶, R⁷ together with the nitrogen atom to which they are attachedvery particularly preferably represent a pyrrolidine, piperidine ormorpholine radical.

[0092] K especially preferably represents oxygen.

[0093] Ar especially preferably represents Ar¹, where Ar¹ representsphenyl which is optionally mono- to trisubstituted by fluorine,chlorine, bromine, methyl, ethyl, propyl, isopropyl, n-, s-, i- ort-butyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butoxy,allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy,methylthio, ethylthio, methylsulphinyl, ethyl-sulphinyl,methylsulphonyl, ethylsulphonyl, trifluoromethyl, difluoro-methoxy,trifluoromethoxy, methylenedioxy, difluoro-methylenedioxy,tetra-fluoroethylenedioxy, difluoromethylthio, trifluoromethylthio,trifluoromethyl-sulphinyl, trifluoromethylsulphonyl, benzyloxy,hydroxyl, nitro, mercapto, cyano or amino, or represents pyridyl whichis optionally mono- or disubstituted by fluorine, chlorine, bromine,methyl, ethyl, methoxy, ethoxy, prop-oxy, i-propoxy or trifluoromethyl,

[0094] or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl or phenoxy, where these substituents for theirpart are optionally mono- or disubstituted by fluorine, chlorine,bromine, methyl, ethyl, isopropyl, n-, s-, i- or t-butyl, methoxy,ethoxy, isopropoxy, n-, s-, i- or t-butoxy, trifluoromethyl,trifluoromethoxy, nitro or cyano.

[0095] Ar most preferably represents phenyl which is mono- orpolysubstituted by trifluoromethyl, fluorine, chlorine, allyloxy, cyano,benzyloxy, or represents the group

[0096]  where particular emphasis is given to the meanings4-chlorophenyl, 3,5-di(trifluoromethyl)phenyl and2-fluoro-4-chloro-5-allyloxy.

[0097] X especially preferably represents CN.

[0098] Y especially preferably represents hydrogen, C₁-C₆-alkyl,C₁-C₃-halogeno-alkyl, cyclopropyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclopentyl-methyl or cyclohexylmethyl.

[0099] Z especially preferably represents hydrogen or methyl.

[0100] Particular mention may also be made of the following sub-group ofcompounds of the formula (I):

[0101] 2-enamino-ketonitriles of the general formula (I)′,

[0102] in which

[0103] K represents oxygen or sulphur,

[0104] Ar represents in each case substituted phenyl, naphthyl orrepresents in each case optionally substituted mono- or bicyclic hetarylhaving 5 to 10 ring atoms,

[0105] X represents CN,

[0106] Y represents hydrogen, represents in each case optionallysubstituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, represents ineach case optionally substituted cycloalkyl or cycloalkylalkyl which isinterrupted in the cycle by heteroatoms or represents optionallysubstituted phenylalkyl or hetarylalkyl,

[0107] Z represents hydrogen, represents in each case optionallysubstituted alkyl, phenyl or phenylalkyl,

[0108] R¹ represents hydrogen, represents in each case optionallysubstituted saturated or unsaturated alkyl or cycloalkyl, each of whichis optionally interrupted by heteroatoms, represents in each caseoptionally substituted phenyl or hetaryl, represents in each caseoptionally substituted phenylalkyl or hetarylalkyl, and

[0109] R² represents hydrogen, represents in each case optionallysubstituted saturated or unsaturated alkyl or alkoxy, represents in eachcase optionally substituted phenyl, phenylalkyl or phenylalkyloxy, or

[0110] R¹, R² furthermore together with the nitrogen atom to which theyare attached may represent an optionally substituted cycle which isoptionally interrupted by one or more heteroatoms.

[0111] For the compounds of the formula (I)′, the following applies:

[0112] Ar preferably represents Ar¹, where Ar¹ represents phenyl,naphthyl or mono- or bicyclic hetaryl having five to ten ring atoms,each of which is optionally mono- to pentasubstituted by halogen,C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkinyl, C₁-C₈-alkoxy,C₂-C₈-alkenyloxy, C₃-C₈-alkinyloxy,C₁-C₈-alkylthio,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkyl,C₁-C₆-halogenoalkoxy, C₂-C₈-halogenoalkenyloxy,C₁-C₂-alkylidenediyl-dioxy, C₁-C₂-halogenoalkyli-denediyl-dioxy,halogeno-C₁-C₄-alkylthio, halogeno-C₁-C₄-alkylsulphonyl, hydroxyl,mercapto, nitro, cyano, amino or by the groups

[0113] or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, naphthyl, five- or six-membered hetaryl,phenyl-C₁-C₄-alkyl, phenoxy, phenyl-S(O)_(g)—, five- or six-memberedhetaryloxy or hetaryl-S(O)_(g), where these substituents for their partare each optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano,where g represents 0, 1 or 2.

[0114] K preferably represents oxygen or sulphur.

[0115] L preferably represents oxygen or sulphur.

[0116] X preferably represents CN,

[0117] Y preferably represents hydrogen, C₁-C₁₂-alkyl, C₃-C₁₀-alkenyl,C₁-C₆-alkoxy-C₂-C₄-alkyl, C₁-C₆-alkylthio-C₂-C₄-alkyl,C₁-C₈-halogeno-alkyl, represents in each case optionally C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl- or halogen-substitutedC₃-C₈-cycloalkyl or C₃-C₈-cyclo-alkyl-C₁-C₄-alkyl, optionallyinterrupted in the cycle by oxygen or sulphur, representsphenyl-C₁-C₄-alkyl or five- or six-membered hetaryl-C₁-C₄-alkyl, each ofwhich is optionally mono- to tetrasubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

[0118] Z preferably represents hydrogen, C₁-C₆-alkyl, represents phenylor phenyl-C₁-C₄-alkyl, each of which is optionally mono- totrisubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano.

[0119] R¹ preferably represents hydrogen, represents in each caseoptionally fluorine and/or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₁₀-alkenyl, C₃-C₆-alkinyl, represents in each case optionallyfluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-substitutedC₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which optionally one methylenegroup may be replaced by oxygen or sulphur, or represents phenyl,pyridyl, thienyl, pyrimidyl, thiazolyl, phenyl-C₁-C₄-alkyl,pyridyl-C₁-C₂-alkyl, thiazolyl-C₁-C₂-alkyl, each of which is optionallymono- to tetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro.

[0120] R² preferably represents hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl.

[0121] R¹, R² furthermore together with the nitrogen atom to which theyare attached preferably represent an in each case optionallyC₁-C₄-alkyl-substituted five- to eight-membered cycle in whichoptionally one methylene group may be replaced by oxygen or sulphur.

[0122] R³ preferably represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkinyl,C₁-C₁₀-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, ineach case optionally fluorine, chlorine, C₁-C₄-alkyl and/orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl or C₃-C₈-cycloalkoxy in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenoxy, benzyloxy, five- or six-membered hetaryl orphenyl-C₁-C₄-alkyl, each of which may optionally be mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, or, in thecase of the radicals a), c) and f) mentioned under Ar, also represents agroup

[0123] R⁴ preferably represents hydrogen or C₁-C₄-alkyl.

[0124] R⁵ preferably represents hydrogen or optionally fluorine- and/orchlorine-substituted C₁-C₄-alkyl.

[0125] R⁶ preferably represents hydrogen, in each case optionallyfluorine- and/or chlorine-substituted C₁-C₁₀-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy, C₃-C₈-alkenyloxy, optionally fluorine-,chlorine-, C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl inwhich optionally one methylene group may be replaced by oxygen orsulphur, represents phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₂-alkoxy,each of which is optionally mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro.

[0126] R⁷ preferably represents hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl.

[0127] R⁶, R⁷ furthermore together with the nitrogen atom to which theyare attached preferably represent an optionally C₁-C₄-alkyl-substitutedfive- to eight-membered cycle in which optionally one methylene groupmay be replaced by oxygen or sulphur.

[0128] For the compounds of the formula (I)′, the following applies:

[0129] K particularly preferably represents oxygen or sulphur.

[0130] Ar particularly preferably represents Ar¹, where Ar¹ representsphenyl, naphthyl, quinolinyl, thienyl, pyrimidyl, furanyl, thiazolyl,benzothiazolyl, oxazolyl, pyrazolyl or pyridyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₁-C₆-alkylthio,C₁-C₄-alkylsulphonyl, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,C₂-C₄-halo-genoalkenyloxy, C₁-C₂-alkylidenediyl-dioxy,C₁-C₂-halogenoalkylidenediyl-dioxy, halogeno-C₁-C₂-alkylthio,halogeno-C₁-C₂-alkylsulphonyl, hydroxyl, mercapto, nitro, cyano, aminoor by one of the following groups

[0131] or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, pyrimidyl, thienyl, furanyl, thiazolyl,tetrazolyl, triazolyl, benzyl, phenoxy, phenyl-S(O)_(g)—, pyridyloxy,pyrimidyloxy, thiazolyloxy, pyridyl-S(O)_(g)—, pyrimidyl-S(O)_(g)— orthiazolyl-S(O)_(g)—, where these substituents for their part areoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₂-C₄-alkenyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, where g represents 0, 1 or 2.

[0132] X particularly preferably represents CN,

[0133] Y particularly preferably represents hydrogen, C₁-C₁₀-alkyl,C₁-C₆-halogeno-alkyl, C₃-C₈-alkenyl, C₁-C₄-alkoxy-C₂-C₃-alkyl,C₁-C₄-alkylthio-C₂-C₃-alkyl, represents optionally C₁-C₄-alkyl-,C₁-C₄-alkoxy-, ₁-C₂-halogenoalkyl-, fluorine- or chlorine-substitutedC₃-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₂-alkyl, representsphenyl-C₁-C₂-alkyl, thiazolylmethyl or pyridylmethyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano or nitro.

[0134] Z particularly preferably represents hydrogen, C₁-C₃-alkyl,represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, ₁-C₂-halogenoalkoxy, nitro or cyano.

[0135] R¹ particularly preferably represents hydrogen, represents ineach case optionally fluorine- and/or chlorine-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl, C₃-C₄-alkinyl, represents optionally fluorine-,chlorine-, C₁-C₂-alkyl-, C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl orrepresents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano or nitro.

[0136] R² particularly preferably represents hydrogen, represents ineach case optionally fluorine- and/or chlorine-substituted C₁-C₄-alkylor C₃-C₄-alkenyl.

[0137] R¹, R² furthermore together with the nitrogen atom to which theyare attached particularly preferably represent an optionallymethyl-substituted five- or six-membered cycle in which optionally onemethylene group may be replaced by oxygen.

[0138] R³ particularly preferably represents in each case optionallyfluorine- and/or chlorine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylthio-C₁-C₂-alkyl, in each case optionally fluorine-,chlorine-, C₁-C₂-alkyl- and/or C₁-C₂-alkoxy-substituted C₃-C₆-cycloalkylor C₃-C₆-cycloalkoxy in which optionally one methylene group may bereplaced by oxygen, represents phenyl, phenoxy, benzyloxy, thienyl,furanyl, pyridyl, pyrimidyl, thiazolyl, pyrazolyl or phenyl-C₁-C₂-alkyl,each of which may optionally be mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄, alkyl, C₁-C₄-alkoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, cyano or nitro, or, in the case ofthe radicals a), c) and f) mentioned under Ar, also represents a group

[0139] R⁴ particularly preferably represents hydrogen.

[0140] R⁵ particularly preferably represents hydrogen, methyl or ethyl.

[0141] R⁶ particularly preferably represents hydrogen, in each caseoptionally fluorine-and/or chlorine-substituted C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, in whichoptionally one methylene group may be replaced by oxygen, representsphenyl or phenyl-C₁-C₂-alkyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro.

[0142] R⁷ particularly preferably represents hydrogen or C₁-C₄-alkyl.

[0143] R⁶, R⁷ furthermore together with the nitrogen atom to which theyare attached particularly preferably represent an optionallyC₁-C₂-alkyl-substituted five- or six-membered cycle in which optionallyone methylene group may be replaced by oxygen.

[0144] For the compounds of the formula (I)′, the following applies:

[0145] K very particularly preferably represents oxygen or sulphur.

[0146] Ar very particularly preferably represents Ar¹, where Ar¹represents phenyl which is optionally mono- to trisubstituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i-or t-butyl, methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy,allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy,methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, trifluoromethyl, difluoro-methoxy, trifluoromethoxy,methylenedioxy, difluoromethylenedioxy, tetra-fluoroethylenedioxy,difluoromethylthio, trifluoromethylthio, trifluoromethyl-sulphinyl,trifluoromethylsulphonyl, hydroxyl, mercapto, nitro, cyano or amino, orrepresents pyridyl which is optionally mono- or disubstituted byfluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, propoxy,i-propoxy, butoxy, i-butoxy, methylthio, ethylthio or trifluoromethyl,or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl orphenoxy, where these substituents for their part are optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- ort-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano.

[0147] X very particularly preferably represents —CN, —CO—NH₂, or

[0148] Y very particularly preferably represents hydrogen, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, allyl, 3-butenyl, C₁-C₄-alkoxy-C₂-alkyl, representsin each case optionally methyl-, methoxy-, trifluoromethyl-, fluorine-or chlorine-substituted cyclopropyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclo-pentylmethyl, cyclohexylmethyl or representsbenzyl which is optionally mono- or disubstituted by fluorine, chlorine,bromine, methoxy, methyl, trifluoromethyl, trifluoromethoxy, cyano ornitro or represents optionally chlorine-substituted pyridylmethyl ortriazolylmethyl.

[0149] Z very particularly preferably represents hydrogen, methyl,ethyl, represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, trifluoro-methoxy, cyano or nitro.

[0150] R³ very particularly preferably represents methyl, ethyl, propyl,isopropyl, n-, s-, i- or t-butyl, vinyl, trifluoromethyl, methoxy,ethoxy, propoxy, isopropoxy, n-, s-, 1- or t-butyloxy, cyclopropyl,cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, representsphenyl, pyridyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, n-, s-, i- ort-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or,in the case of the radicals a), c) and f) mentioned under Ar, alsorepresents a group

[0151] R⁵ very particularly preferably represents hydrogen or methyl.

[0152] R⁶ very particularly preferably represents hydrogen, methyl,ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl,cyclopentyl, cyclohexyl, represents phenyl which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro.

[0153] R⁷ very particularly preferably represents hydrogen, methyl orethyl.

[0154] R⁶, R⁷ together with the nitrogen atom to which they are attachedvery particularly preferably represent a pyrrolidine, piperidine ormorpholine radical.

[0155] For the compounds of the formula (I)′, the following applies:

[0156] K especially preferably represents oxygen.

[0157] Ar especially preferably represents Ar¹, where Ar¹ representsphenyl which is optionally mono- to trisubstituted by fluorine,chlorine, bromine, methyl, ethyl, propyl, isopropyl, n-, s-, i- ort-butyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butoxy,allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy,methylthio, ethylthio, methylsulphinyl, ethyl-sulphinyl,methylsulphonyl, ethylsulphonyl, trifluoromethyl, difluoro-methoxy,trifluoromethoxy, methylenedioxy, difluoromethylenedioxy,tetra-fluoroethylenedioxy, difluoromethylthio, trifluoromethylthio,trifluoromethyl-sulphinyl, trifluoromethylsulphonyl, hydroxyl, nitro,mercapto, cyano or amino or represents pyridyl which is optionally mono-or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, methoxy,ethoxy, propoxy, i-propoxy or trifluoromethyl,

[0158] or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl or phenoxy, where these substituents for theirpart are optionally mono- or disubstituted by fluorine, chlorine,bromine, methyl, ethyl, isopropyl, n-, s-, i- or t-butyl, methoxy,ethoxy, isopropoxy, n-, s-, i- or t-butoxy, trifluoromethyl,trifluoromethoxy, nitro or cyano.

[0159] X especially preferably represents CN.

[0160] Y especially preferably represents hydrogen, C₁-C₆-alkyl,C₁-C₃-halogeno-alkyl, cyclopropyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclopentyl-methyl or cyclohexylmethyl.

[0161] Z especially preferably represents hydrogen or methyl.

[0162] All of the abovementioned compounds of the formula (I) can bepresent both as cis and as trans isomers. To simplify the presentation,in each case only one isomer is shown in the formulae of the compounds.However, the respective other isomer is likewise included in theinvention.

[0163] The abovementioned general or preferred radical definitions applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials and intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

[0164] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred (preferable).

[0165] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0166] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0167] Especial preference according to the invention is given to thecompounds of the formula (I) which contain a combination listed above asbeing especially preferred.

[0168] Saturated or unsaturated hydrocarbon radicals, such as alkyl oralkenyl, can in each case be straight-chain or branched as far as thisis possible, including in combination with heteroatoms, such as, forexample, in alkoxy.

[0169] Unless indicated otherwise, optionally substituted radicals canbe mono- or polysubstituted, where in the case of polysubstitution, thesubstituents can be identical or different.

[0170] It has been found that the novel compounds of the formula (I) areobtained by the process described below:

[0171] (A) compounds of the formula (I)

[0172]  in which

[0173] Ar, X, Y and Z are each as defined above and

[0174] K represents oxygen

[0175]  are obtained when

[0176] compounds of the formula (II)

[0177]  in which

[0178] Ar and X are each as defined above,

[0179]  are reacted with compounds of the formula (III)

[0180]  in which

[0181] Y and Z are each as defined above but do not represent hydrogenand

[0182] W represents O or S(O)_(g), where g represents 0 or 2, and

[0183] R⁸ represents alkyl, in particular C₁-C₆-alkyl, or benzyl, ifappropriate in the presence of a diluent and if appropriate in thepresence of a base or an acid and/or a metal compound of the formula(IV)

Me(V)₂  (IV)

[0184]  in which

[0185] Me represents a divalent transition metal atom, in particularnickel, and

[0186] V represents a chelate ligand, in particular a bidentate chelateligand, such as, for example, acetylacetonate (R. G. Glushkov et al.,Khim.-Farm. Zh. 24, (7), (1990), 24-27; M. V. Mezentseva et al.,Khim.-Farm. Zh. 25,(12), (1991), 19-23; G. Dannhardt, A. Bauer,Pharmazie 51,(1996), 805-810).

[0187] (B) Moreover, it has been found that compounds of the formula (I)

[0188]  in which

[0189] Ar, X, Y and Z are each as defined above and

[0190] K represents oxygen,

[0191]  are obtained when compounds of the formula (V)

[0192]  in which

[0193] Ar and X are each as defined above, and

[0194] Hal represents halogen, in particular chlorine or bromine,

[0195]  are reacted with compounds of the formula (VI)

[0196]  in which

[0197] Y and Z are each as defined above, but do not represent hydrogen,

[0198]  if appropriate in the presence of a diluent, to give compoundsof the formula

[0199]  in which

[0200] Ar, X, Y and Z are each as defined above

[0201] which are reacted further, if appropriate in the presence of abase and if appropriate in the presence of a trivalent phosphoruscompound (for example triphenylphosphine, triethyl phosphite), withelimination of sulphur and hydrogen halide, to give compounds of theformula (I)

[0202]  in which

[0203] Ar, X, Y and Z are each as defined above

[0204]  (see A. Eschenmoser et al., Helv. Chim. Acta 54, (1971),710-734; V. Issartel et al., C.R. Acad. Sci., Ser. II, Mec., Phys.,Chim., Astron. 321, (12), (1995), 521-524).

[0205] (C) Furthermore, it has been found that compounds of the formula(I)

[0206]  in which

[0207] Ar, X, Y and Z are each as defined above and K represents oxygen,

[0208]  are obtained when compounds of the formula (II)

[0209]  in which

[0210] Ar and X are each as defined above,

[0211]  are initially condensed with compounds of the formula (VIII)

[0212]  in which

[0213] Z is as defined above and

[0214] R⁹ represents C₁-C₄-alkyl, preferably methyl and ethyl, and theresulting intermediates are, preferably without intermediate isolation,reacted with amines of the formula (IX)

Y—NH₂  (IX)

[0215]  in which

[0216] Y is as defined above,

[0217]  if appropriate in the presence of a diluent and if appropriatein the presence of a base.

[0218] (D) Furthermore, it has been found that compounds of the formula(I)

[0219]  in which

[0220] Ar, X, Y and Z are each as defined above and

[0221] K represents sulphur,

[0222]  are obtained when compounds of the formula (I)

[0223]  in which

[0224] Ar, X, Y and Z are each as defined above and

[0225] K represents oxygen

[0226]  are reacted in the presence of a sulphurizing agent, such as,for example, phosphorus pentasulphide or2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiaphosphetane 2,4-disulphide(Lawesson's reagent) in the presence of a solvent.

[0227] (E) Moreover, it has been found that compounds of the formula (I)

[0228]  in which

[0229] Ar, X, Y and Z are each as defined above,

[0230] Ar has the meaning given above for Ar² and

[0231] K represents oxygen,

[0232]  are obtained when compounds of the formula (I¹)

[0233]  in which

[0234] Ar¹, X, Y and Z are each as defined above and

[0235] Hal represents halogen, in particular bromine,

[0236]  are reacted with boronic acids of the formula (X)

A—B(OH)₂  (X)₂

[0237]  in which

[0238] Ar^(2′) represents the substituents which have been mentionedabove under Ar² as additional substituents for Ar¹,

[0239]  in the presence of a solvent, if appropriate in the presence ofa base and a noble metal complex, preferably a palladium complex.

[0240] Using, according to process A, for example4-methyl-benzoylacetonitrile and methyl N-ethyliminoacetate as startingmaterials, the course of the reaction can be represented by thefollowing reaction scheme:

[0241] Using, according to process B, for example2-bromo-2-(3-chlorobenzoyl)acetonitrile and N-methylthiobenzamide asstarting materials, the course of the reaction can be represented by thefollowing reaction scheme:

[0242] Using, according to process C, for example3,4-dichloro-benzoyl-acetonitrile, methyl orthoacetate andisopropylamine as starting materials, the course of the reaction can berepresented by the following reaction scheme:

[0243] Using, according to process D, for exampleZ-2-(4-trifluoromethyl-benzoyl)-3-(N-ethylamino)crotononitrile andLawesson's reagent as starting materials, the course of the reaction canbe represented by the following reaction scheme:

[0244] Using, according to process E, for example2-(4-bromo-benzoyl)-3-(N-methylamino)crotononitrile and4-chloro-phenylboronic acid as starting materials, the course of thereaction can be represented by the following reaction scheme:

[0245] The compounds of the formula (II)

[0246] in which

[0247] Ar, X are each as defined above,

[0248] required as starting materials in process (A) are known or can beprepared by processes known in principle from the literature (Organikum,16th revised edition, pp. 415, 417, VEB Deutscher Verlag derWissenschaften, Berlin 1986, German Patent Applications with theapplication numbers 198 519 86 and 10 007 286 and WO 00/27 812).

[0249] The compounds of the formula (II) are obtained, for example, byhydrolysing compounds of the formula (XI)

[0250] in which

[0251] Ar is as defined above,

[0252] R¹⁰ represents alkyl, in particular C₁-C₆-alkyl, or benzyl, whichmay optionally be substituted,

[0253] in the presence of an acid (for example an inorganic acid, suchas hydrochloric acid) or a base (for example an alkali metal hydroxide,such as sodium hydroxide or potassium hydroxide) and if appropriate inthe presence of a diluent (for example an aqueous alcohol, such asmethanol or ethanol), at temperatures between 0° C. and 200° C.,preferably between 20° C. and 150° C., followed by decarboxylation,where the elimination of the radical may optionally also be carried outhydrolytically by known processes (Bowman, Fordham, J. Chem. Soc. 1951,2758) using molecular hydrogen at pressures between 1 and 100 bar, ifappropriate in the presence of a solvent, such as, for example,methanol, ethanol or ethyl acetate, at temperatures between −20 and 100°C., preferably at room temperature, in the presence of a transitionmetal, such as, for example, palladium, nickel, rhodium or platinum,which is optionally immobilized on a support, such as, for example,activated carbon or barium sulphate.

[0254] The compounds of the formula (XI) can be prepared by knownprocesses (Organikum, 16th revised edition, p. 480, VEB Deutscher Verlagder Wissen-schaften, Berlin 1986).

[0255] The compounds of the formula (XI) are obtained, for example, byreacting compounds of the formula (XII)

[0256] in which

[0257] Ar is as defined above,

[0258] with cyanoacetic acid esters of the formula (XIII)

[0259] in which

[0260] R¹⁰ represents alkyl, in particular C₁-C₆-alkyl, or benzyl,

[0261] in the presence of a base (for example a metal alkoxide, such assodium methoxide or sodium ethoxide) and if appropriate in the presenceof a diluent (for example ether or the alcohol which is derived from thealkoxide), at temperatures of from 0° C. to 150° C., preferably between20 and 120° C.

[0262] Some of the compounds of the formula (XII) are novel, and theycan be prepared by processes known in principle (for example Organikum,16th revised edition, p. 423, VEB Deutscher Verlag der Wissenschaften,Berlin 1986).

[0263] The compounds of the formula (XII) are obtained, for example, byreacting compounds of the formula (XIV)

[0264] in which

[0265] Ar is as defined above,

[0266] with halogenating agents (for example thionyl chloride, phosgene,phosphorus trichloride), if appropriate in the presence of a diluent(for example optionally chlorinated aliphatic or aromatic hydrocarbons,such as toluene or methylene chloride), at temperatures of from 0° C. to150° C., preferably between 20° C. and 100° C.

[0267] Cyanoacetic acid esters of the formula (XIII) are known compoundsof organic chemistry.

[0268] Some of the compounds of the general formula (XIV-b)

[0269] in which

[0270] B¹⁰ represents hydrogen or fluorine and

[0271] B⁸ represents hydrogen, hydroxyl, represents in each caseoptionally cyano-, halogen-, alkoxy-, alkylcarbonyl- oralkoxycarbonyl-substituted alkyl, alkyl-carbonyl alkoxycarbonyl,alkylthio or alkylsulphonyl, represents in each case optionallyhalogen-substituted alkenyl or alkinyl, represents in each caseoptionally halogen- or alkyl-substituted cycloalkyl or cycloalkylalkyl,represents in each case optionally halogen-substituted alkoxy oralkenyloxy, represents in each case optionally cyano-, halogen-, alkyl-,halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyl orarylalkoxy,

[0272] are known, or they can be synthesized by known processes.

[0273] Here, B⁸ preferably represents hydrogen, hydroxyl, represents ineach case optionally cyano-, halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylcarbonyl- or C₁-C₄-alkoxycarbonyl-substituted C₁-C₈-alkyl,C₁-C₈-alkylcarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-alkylthio orC₁-C₈-alkylsulphonyl, represents in each case optionallyhalogen-substituted C₂-C₆-alkenyl or C₂-C₆-alkinyl, represents in eachcase optionally halogen- or C₁-C₄-alkyl-substituted C₃-C₈-cycloalkyl orC₃-C₈-cycloalkyl-C₁-C₄-alkyl, represents in each case optionallyhalogen-substituted C₁-C₈-alkoxy or C₂-C₈-alkenyloxy, represents in eachcase optionally cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkoxy-substituted phenyl-C₁-C₄-alkyl orpenyl-C₁-C₄-alkoxy.

[0274] The novel compounds are obtained, inter alia, by convertingcompounds of the general formula (XV)

[0275] in which

[0276] B¹ represents hydrogen or fluorine and

[0277] B⁸ is as defined above,

[0278] by processes known per se using CO₂ in the presence oforganometallic compounds into compounds of the general formula (XIV-b)(for example Organikum, 16th revised edition, p.⁴99, VEB DeutscherVerlag der Wissenschaften 1986).

[0279] Suitable for use as organometallic bases are, in addition toorganomagnesium compounds, also organolithium compounds, which are knownchemicals for synthesis of organic chemistry. Suitable solvents/diluentsare hydrocarbons (such as toluene) or ethers (such as, for example,tetrahydrofuran or diethyl ether). It is also possible to use mixturesof the abovementioned solvents.

[0280] The reaction temperature is usually between −100° C. and 80° C.,preferably between −80° C. and 25° C. (room temperature). For work-up,the reaction mixture is diluted with water or an inorganic acid, suchas, for example, hydrochloric acid, which may be diluted orconcentrated, and the product is isolated using a water-immisciblesolvent and purified by customary methods, for example bycrystallization.

[0281] Some of the compounds of the general formula (XV) in which

[0282] B¹ represents hydrogen or fluorine and

[0283] B⁸ is as defined above,

[0284] are novel, and they can be synthesized by known processes (Sickeret al., Tetrahedron, 31, (1996), 10389; Bell et al., J. Med. Chem., 33,(1990), 380).

[0285] The novel compounds of the formula (XV) in which

[0286] B¹ represents hydrogen or fluorine and

[0287] B⁸ represents in each case optionally cyano-, halogen-, alkoxy-,alkylcarbonyl- or alkoxycarbonyl-substituted alkyl, alkylcarbonyl,alkoxycarbonyl, alkylthio or alkylsulphonyl, represents in each caseoptionally halogen-substituted alkenyl or alkinyl, represents in eachcase optionally halogen- or alkyl-substituted cycloalkyl orcycloalkylalkyl, represents in each case optionally cyano-, halogen-,alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyl,

[0288] are obtained, inter alia, from compounds of the general formula(XV)′

[0289] in which B¹ represents hydrogen or fluorine and B⁹ representshydrogen, by reaction with an alkylating agent of the formula (XVI)

B⁸—X¹  (XVI),

[0290] in which

[0291] B⁸ represents in each case optionally cyano-, halogen-, alkoxy-,alkylcarbonyl- or alkoxycarbonyl-substituted alkyl, alkylcarbonyl,alkoxycarbonyl, alkylthio or alkylsulphonyl, represents in each caseoptionally halogen-substituted alkenyl or alkinyl, represents in eachcase optionally halogen- or alkyl-substituted cycloalkyl orcycloalkylalkyl, represents in each case optionally cyano-, halogen-,alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyland

[0292] X¹ represents halogen, in particular iodine, bromine or chlorine,or other leaving groups, for example activated esters, such as mesylateor tosylate, or

[0293] from compounds of the general formula (XV)′ in which B¹represents hydrogen or fluorine and B⁹ represents hydroxyl, by reactionwith an alkylating agent of the formula (XVII)′

B¹⁰−X¹  (XVII)′,

[0294] in which

[0295] B¹⁰ represents in each case optionally halogen-substituted alkylor alkenyl or represents in each case optionally cyano-, halogen-,alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyland

[0296] X¹ represents halogen, in particular iodine, bromine or chlorine,or other leaving groups, for example activated esters, such as mesylateor tosylate,

[0297] if appropriate in the presence of a base and in the presence of asolvent.

[0298] Bases suitable for use in the reaction are, in addition to alkalimetal oxides and alkaline earth metal oxides, tertiary amines, such astriethylamine, pyridine or N,N-diethylaniline, which may be used inmolar ratios or else in excess.

[0299] Suitable solvents or diluents are, in addition to hydrocarbonssuch as toluene, also halogenated hydrocarbons, such as dichloromethane.It is possible to use polar aprotic solvents/diluents, such asdimethylformamide, and also mixtures of the abovementioned solvents. Thereaction temperature is usually between the melting point and theboiling point of the reaction mixture, preferably between −10° C. and80° C.

[0300] The compounds of the general formula (XV)′, in which B¹represents hydrogen or fluorine and B⁹ represents hydrogen are knownfrom the literature (Huang et al., Synthesis (1984), 851; JP 63132881)and can be converted by oxidation according to processes known per seinto compounds of the general formula (XV)′ in which B¹ representshydrogen or fluorine and B⁹ represents hydroxyl (P. G. Sammes et al., J.Chem. Soc., Perkin Trans I, (1979), 2481).

[0301] Furthermore, compounds of the general formula (XIV-b) in which

[0302] B¹ represents hydrogen or fluorine and

[0303] B⁸ is as defined above,

[0304] can be obtained by hydrolysing compounds of the formula (XVIII)

[0305] in which

[0306] B¹ represents hydrogen or fluorine,

[0307] B⁸ is as defined above and

[0308] B¹ represents alkyl or benzyl, in particular C₁-C₆-alkyl orbenzyl, which may optionally be fully or partially substituted by theradicals R¹ or R²,

[0309] in the presence of an acid (for example an inorganic acid, suchas hydrochloric acid) or a base (for example an alkali metal hydroxide,such as sodium hydroxide or potassium hydroxide) and if appropriate inthe presence of a diluent (for example an aqueous alcohol, such asmethanol or ethanol), at temperatures between 0° C. and 200° C.,preferably between 20° C. and 150° C. The radical B¹¹ can optionallyalso be removed hydrogenolytically using molecular hydrogen at pressuresbetween 1 and 100 bar, if appropriate in the presence of a solvent, forexample methanol, ethanol or ethyl acetate, at temperatures between −10°C. and 100° C., preferably at room temperature, in the presence of atransition metal, for example palladium, nickel, rhodium or platinum,which may optionally be immobilized on a support, such as activatedcarbon or barium sulphate, using known processes (Bowman, Fordham J.Chem. Soc., 1951, 2758).

[0310] Furthermore, compounds of the general formula (XVIII) in which

[0311] B¹ represents hydrogen or fluorine and

[0312] B⁸ is as defined above and

[0313] B¹¹ represents hydrogen, alkyl or benzyl, in particularC₁-C₆-alkyl or benzyl, which may optionally in each case be fully orpartially substituted by the radicals R¹ or R²,

[0314] can be obtained according to customary processes known per se, byreacting compounds of the general formula (XV) in which

[0315] B¹ represents hydrogen or fluorine and

[0316] B⁸ is as defined above,

[0317] with a nucleophile of the general formula (XIX)

[0318] in which

[0319] B¹¹ represents hydrogen, alkyl or benzyl, in particularC₁-C₆-alkyl or benzyl, which may optionally in each case be fully orpartially substituted by the radicals R¹ or R²,

[0320] in the presence of CO at pressures of from 1 bar to 100 bar,preferably between 1 bar and 50 bar, and at temperatures between 20° C.and 300° C., preferably between 20° C. and 150° C., in the presence of acatalyst, for example palladium salts or cobalt salts or transitionmetal carbonyl compounds, such as, for example, Co₂(CO)₈, if appropriatein the presence of a ligand (such as, for example, triphenylphosphine,trisodium (3-sulphonylphenyl)phosphine, in the presence of a base (forexample an alkali metal hydroxide, such as sodium hydroxide or potassiumhydroxide, or else organic bases, such as triethylamine or pyridine) andof a diluent (for example alcohols, water, tetrahydrofuran,dichloromethane, toluene or mixtures of the abovementioned diluents).The reaction can optionally also be carried out in the presence ofphase-transfer catalysts (for example glycols, crown ethers or ammoniumsalts, such as tetrabutylammonium bromide or chloride) or auxiliaries(for example zeolites) or under irradiation with light, according toknown processes (Ziolkowski et al., J. Mol. Catal. A: Chem., 154,(2000), 93; P. Kalck et al., J. Organomet. Chem., 482, (1994), 45; DuPont de Nemours & Co U.S. Pat. No. 2,734,912; Alper, H. et al., Angew.Chem., 96, (1984), 710; Takatori K. et al., Tetrahedron, 54, (1998),15861).

[0321] Furthermore, compounds of the general formula (XIV-b)

[0322] in which

[0323] B¹ represents hydrogen or fluorine and

[0324] B⁸ represents in each case optionally cyano-, halogen-, alkoxy-,alkylearbonyl- or alkoxycarbonyl-substituted alkyl, alkylcarbonyl,alkoxycarbonyl, alkylthio or alkylsulphonyl, represents in each caseoptionally halogen-substituted alkenyl or alkinyl, represents in eachcase optionally halogen- or alkyl-substituted cycloalkyl orcycloalkylalkyl, represents in each case optionally cyano-, halogen-,alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyl,

[0325] can be obtained from compounds of the general formula (XIV-b),

[0326] in which

[0327] B¹ represents hydrogen or fluorine and

[0328] B⁸ represents hydrogen,

[0329] by reaction with an alkylating agent of the formula (XVII)′

B¹⁰−X¹  (XVII)′

[0330] in which

[0331] B¹⁰ represents in each case optionally halogen-substituted alkylor alkenyl or represents in each case optionally cyano-, halogen-,alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyland

[0332] X¹ represents halogen, in particular iodine, bromine or chlorine,or other leaving groups, for example activated esters, such as mesylateor tosylate,

[0333] if appropriate in the presence of a base and in the presence of asolvent.

[0334] Bases suitable for use in the reaction are, in addition to alkalimetal oxides and alkaline earth metal oxides, tertiary amines such astriethylamine, pyridine or N,N-diethylaniline, which can be used inmolar ratios or else in excess. Suitable solvents are, in addition tohydrocarbons such as toluene, also halogenated hydrocarbons, such asdichloromethane. It is possible to use polar aprotic solvents/diluents,such as dimethylformamide, and also mixtures of the abovementionedsolvents. The reaction temperature is usually between the melting pointand the boiling point of the reaction mixture, preferably between −10°C. and 80° C.

[0335] Some of the compounds of the formula (III)

[0336] in which

[0337] W, Y, Z and R⁸ are each as defined above,

[0338] likewise required as starting materials are known, and they canbe prepared by known processes (see Example III-a-1 and H. Bredereck, F.Effenberger, E. Henseleit, Chem. Ber. 1965, 98, 2754; P. Deslongchamps,O. C. Ukken, A. Guida, R. J. Taillefer,

[0339] Nouv. J. Chim. 1977, 235, 240; R. M. Moriarty, C. L. Yeh, K. C.Ramey, P. W.

[0340] Whiteburst, J. Am. Chem. Soc. 1970, 21, 6360).

[0341] Some of the compounds of the formula (V)

[0342] in which

[0343] Ar and Hal are each as defined above and X represents cyano,

[0344] are known, or they can be prepared by known processes (Gakhar H.K. et. al, J. Indian Chem. Soc. 43 (1971) 953; Corsaro A. Heterocycles23 (1985) 2645).

[0345] The compounds of the formula (VI)

[0346] in which

[0347] Z and Y are each as defined above,

[0348] are compounds of organic chemistry which are known in principle,and some are commercially available (see also Preparation Example 5).

[0349] The compounds of the formula (VIII)

[0350] in which

[0351] Z and R⁹ are each as defined above,

[0352] are compounds of organic chemistry which are known in principle,and some of them are commercially available.

[0353] Most of the compounds of the formula (IX) are commerciallyavailable compounds, or they can be prepared by generally knownprocesses of organic chemistry.

[0354] Some of the arylboronic acids of the formula (X) required forcarrying out process E are commercially available, or they can beprepared by known processes.

[0355] Suitable diluents for process (A) are all organic solvents whichare inert towards the reactants. Preference is given to using optionallychlorinated aliphatic or aromatic hydrocarbons, such as toluene, xylene,mesitylene, chlorobenzene, chloroform, methylene chloride, furthermorepolar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide, dimethylacetamide or N-methylpyrrolidone. It is alsopossible to use ethers, such as diethyl ether, tetrahydrofuran ordioxane.

[0356] Bases suitable for use in process (A) are all customary acidacceptors which do not hydrolyse the reactants.

[0357] Preference is given to use tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN) orN,N-dimethylaniline.

[0358] Acids suitable for use in process (A) are all acids which do nothydrolyse the reactants. Preference is given to using organic acids,such as p-toluenesulphonic acid and trifluoroacetic acid.

[0359] When carrying out process (A), the reaction temperatures can bevaried within a relatively wide range. The process is expedientlycarried out at temperatures between −20° C. and 160° C., preferablybetween 0° C. and 120° C.

[0360] The process (A) is preferably carried out under atmosphericpressure. When carrying out process (A), the reaction component offormula (III) is employed in equimolar amounts or in a relatively largeexcess (up to 5 mol), preferably in 1.5 to 2 times the molar amount,based on the reaction component of the formula (II).

[0361] The base which is optionally employed is preferably used in anamount which is equimolar to that of the reaction component of theformula (II). The acid that is employed, if appropriate, is preferablyused in catalytic amounts.

[0362] The process (B) is characterized in that compounds of the formula(V) are in each case reacted with thioamides of the formula (VI), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

[0363] The starting materials of the formula (V) can be prepared byknown processes (Gakhar H. K. et al., J. Indian Chem. Soc. 43, (1971),953 or Corsaro A., Heterocycles 23, (1985), 2645). The compounds of theformula (VI) can be prepared from the corresponding keto compound usingthionylating agents, in particular Lawesson's reagent, in inertsolvents, such as, for example, toluene (see Preparation Example 5).

[0364] Diluents suitable for use in the process (B) according to theinvention are all solvents which are inert towards the compounds of theformula (V). Preference is given to using hydrocarbons, such as benzine,benzene, toluene, xylene and tetralin, furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylic acidesters, such as ethyl acetate, and also strongly polar solvents, such asdimethylformamide, N-methylpyrrolidone, dimethyl sulphoxide andsulpholane.

[0365] Suitable acid binders for the reaction according to process (B)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hunig base and N,N-dimethylaniline, polymericbases, such as diisopropylaminopolystyrene, furthermore alkaline earthmetal oxides, such as magnesium oxide and calcium oxide, moreover alkalimetal carbonates and alkaline earth metal carbonates, such as sodiumcarbonate, potassium carbonate and calcium carbonate, and also alkalimetal hydroxides, such as sodium hydroxide and potassium hydroxide.

[0366] Phosphorus reagents suitable for use in the process (B) accordingto the invention are alkyl phosphites, such as triethyl phosphite,tributyl phosphite, or triphenylphosphines, such as triphenylphosphine.

[0367] The reaction temperature in the process (B) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between 0° C. and 200° C.,preferably between +20° C. and 150° C.

[0368] When carrying out the process (B) according to the invention, thestarting materials of the formula (V) and the thioamide of the formula(VI) are generally each employed in approximately equivalent amounts.However, it is also possible to use a relatively large excess of onecomponent or the other. Work-up is carried out by customary methods.

[0369] The process (C) is characterized in that initially compounds ofthe formula (II) are condensed with orthoesters of the formula (VIII),and the resulting condensates are, without intermediatecharacterization, reacted with amines of the formula (IX).

[0370] Acid binders suitable for the reaction according to the process(C) according to the invention are, if appropriate, all customary acidacceptors. Preference is given to using tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hunig base andN,N-dimethylaniline, polymeric bases, such as, for example,disopropylaminopolystyrene, furthermore alkaline earth metal oxides,such as magnesium oxide and calcium oxide, moreover alkali metalcarbonates and alkaline earth metal carbonates, such as sodiumcarbonate, potassium carbonate and calcium carbonate, and also alkalimetal hydroxides, such as sodium hydroxide and potassium hydroxide.

[0371] Diluents suitable for the process (C) according to the inventionare all solvents which are inert towards the orthoesters. Preference isgiven to using hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenated hydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic acid esters, suchas ethyl acetate, moreover nitrites such as acetonitrile, and alsostrongly polar solvents, such as dimethylformamide, dimethylacetamide,N-methylpyrrolidone, dimethyl sulphoxide and sulpholane. According to afurther process variant, the orthoesters themselves may also be used assolvents. This process variant is emphasized as being preferred.

[0372] The reaction temperature in the process (C) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and 200° C.,preferably between 0° C. and 150° C.

[0373] The process (C) according to the invention is generally carriedout under atmospheric pressure.

[0374] When carrying out the process (C) according to the invention, thestarting materials of the formula (II) and the appropriate amine of theformula (IX) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 10 mol, preferably up to 3 mol) of one component or the other.The orthoesters of the formula (VIII) are generally employed in arelatively large excess. Work-up is carried out according to customarymethods by concentrating the reaction mixture by removing the diluentand excess reactants under reduced pressure and purifying the residuefurther.

[0375] The process (D) is characterized in that compounds of the formula(I) in which Ar, X, Y and Z are each as defined above and K representsoxygen are reacted with sulphurizing agents, if appropriate in thepresence of a diluent.

[0376] The sulphurizing agents to be used are known chemicals forsynthesis, such as, for example, phosphorus pentasulphide or2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiaphos-phetane 2,4-disulphide(Lawesson's reagent).

[0377] Diluents suitable for use in the process (D) according to theinvention are all solvents which are inert towards the abovementionedreagents. Preference is given to using hydrocarbons, such as benzine,benzene, toluene, xylene and tetralin, furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, chlorobenzene ando-dichlorobenzene, ethers, such as tetrahydrofuran, dioxane, diisopropylether or methyl tert-butyl ether.

[0378] In the process (D) according to the invention, the reactiontemperatures can be varied within a relatively wide range.

[0379] In general, the process is carried out at temperatures between 0°C. and 250° C., preferably between 40° C. and 200° C.

[0380] When carrying out the process (D) according to the invention, thestarting materials of the formula (I) and the abovementioned reagentsare generally each employed in approximately equivalent amounts.However, it is also possible to use a relatively large excess of up to 5mol of the abovementioned reagents. Work-up is carried out by customarymethods.

[0381] Some of the arylboronic acids required for carrying out theprocess (E), such as, for example, 4-chloro-phenylboronic acid, arecommercially available, or they can be prepared by known processes.

[0382] Suitable acid acceptors for carrying out the process (E)according to the invention are inorganic or organic bases. Thesepreferably include alkaline earth metal hydroxides, acetates, carbonatesor bicarbonates or alkali metal hydroxides, acetates, carbonates orbicarbonates, such as, for example, sodium hydroxide, potassiumhydroxide, barium hydroxide or ammonium hydroxide, sodium acetate,potassium acetate, calcium acetate or ammonium acetate, sodiumcarbonate, potassium carbonate or ammonium carbonate, sodium bicarbonateor potassium bicarbonate, alkali metal fluorides, such as, for example,caesium fluoride, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethylaminopyridine, diazabicyclooctane(DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN).

[0383] Suitable diluents for carrying out the process (E) according tothe invention are water, organic solvents and any mixtures thereof.Examples which may be mentioned are: aliphatic, alicyclic or aromatichydrocarbons, such as, for example, petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin;halogenated hydrocarbons, such as, for example, chlorobenzene,dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride,dichloroethane, trichloroethane or tetrachloroethylene; ethers, such asdiethyl ether, diisopropyl ether, methyl tert-butyl ether, methyltert-amyl ether, dioxane, tetra-hydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane, diethylene glycol dimethyl ether or anisole;alcohols, such as methanol, ethanol, n- or i-propanol, n-, iso-, sec- ortert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,methoxyethanol, di-ethylene glycol monomethyl ether, diethylene glycolmonoethyl ether; water.

[0384] The reaction temperature in the process (E) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between 0° C. and +200° C.,preferably between 50° C. and +1 50° C.

[0385] When carrying out the process (E) according to the invention, theboronic acid of the formula (X) in which Ar^(2′) is as defined above andcompounds of the formula (I¹) in which Ar¹, K, X, Y, Z and Hal are eachas defined above are employed in a molar ratio of from 1:1 to 3:1,preferably from 1:1 to 2:1. The catalyst is generally employed inamounts of from 0.005 to 0.5 mol, preferably from 0.01 to 0.1 mol, permole of the compound of the formula (I¹). The base is generally employedin excess.

[0386] The active compounds according to the invention are particularlysuitable for use as defoliants, desiccants, haulm-killers and,especially, as weed-killers. By weeds, in the broadest sense, are to beunderstood all plants which grow in locations where they are undesired.Whether the substances according to the invention act as total orselective herbicides depends essentially on the amount used. The dosagesof the active compounds according to the invention required for weedcontrol are between 0.001 and 10 kg/ha, preferably between 0.005 and 5kg/ha.

[0387] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0388] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0389] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0390] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0391] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

[0392] According to the invention, it is possible to treat all plantsand parts of plants. By plants are to be understood here all plants andplant populations such as. desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

[0393] The treatment of the plants and parts of plants according to theinvention with the active compounds is carried out directly or by actionon their environment, habitat or storage area according to customarytreatment methods, for example by dipping, spraying, evaporating,atomizing, broadcasting, brushing-on and, in the case of propagationmaterial, in particular in the case of seeds, furthermore by one- ormulti-layer coating.

[0394] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants. With respect to the use of the activecompounds according to the invention, particular emphasis is given tothe use in connection with transgenic plants since in this casesynergistically enhanced activities may be observed.

[0395] The compounds are suitable, depending on the concentration, forthe total control of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial cultures, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, onlawns, turf and pasture-land, and for the selective control of weeds inannual crops.

[0396] The active compounds according to the invention are highlysuitable for the selective control of monocotyledonous weeds indicotyledonous crops by the pre- and post-emergence method. They can beused very successfully, for example, for the control of harmful grassesin cotton or sugar beet.

[0397] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting agents, pastes, soluble powders, granules,suspo-emulsion concentrates, natural and synthetic materials impregnatedwith active compound and very fine capsules in polymeric substances.

[0398] These formulations are prepared in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, if appropriate with the use of surfactants, thatis emulsifiers and/or dispersants and/or foam-formers.

[0399] If the extender used is water, it is also possible to use, forexample, organic solvents as auxiliary solvents. Suitable liquidsolvents are essentially: aromatics, such as xylene, toluene, oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample mineral oil fractions, mineral or vegetable oils, alcohols, suchas butanol or glycol, and also their ethers and esters, ketones, such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, and also water.

[0400] Suitable solid carriers are: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,as well as synthetic granules of inorganic and organic meals, andgranules of organic material such as sawdust, coconut shells, maize cobsand tobacco stalks; suitable emulsifiers and/or foam-formers are: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

[0401] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

[0402] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0403] The formulations in general contain between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%, and in additionpreferably extenders and/or surfactants.

[0404] The active compound according to the invention can be present inits commercially available formulations and in the use forms, preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilizing agents, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms, inter alia. In preferred embodiments of the presentinvention, it is also possible to mix safeners with the compoundsaccording to the invention, to increase crop plant compatibility.

[0405] Examples of particularly advantageous mixing components are thefollowing:

[0406] Fungicides:

[0407] aldimorph, ampropylfos, ampropylfos potassium, andoprim,anilazine, azaconazole, azoxystrobin,

[0408] benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

[0409] calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0410] debacarb, dichlorophen, diclobutrazole, diclofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine,dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0411] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

[0412] famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

[0413] guazatine,

[0414] hexachlorobenzene, hexaconazole, hymexazole,

[0415] imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

[0416] kasugamycin, kresoxim-methyl, copper preparations, such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0417] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0418] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0419] ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,oxyfenthiin,

[0420] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

[0421] quinconazole, quintozene (PCNB),

[0422] sulphur and sulphur preparations,

[0423] tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemotph,triflumizole, triforine, triticonazole,

[0424] uniconazole,

[0425] validamycin A, vinclozolin, viniconazole,

[0426] zarilamide, zineb, ziram and also

[0427] Dagger G,

[0428] OK-8705,

[0429] OK-8801,

[0430]α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0431]α-(2,4-dichlorophenyl)-β-fluoro-propyl-1H-1,2,4-triazole-1-ethanol,

[0432]α-(2,4-dichlorophenyl)-β-methoxy-methyl-1H-1,2,4-triazole-1-ethanol,

[0433]α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0434](5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

[0435] (E)-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0436] 1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

[0437] 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanoneO-(phenylmethyl)-oxime,

[0438] 1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

[0439] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

[0440] 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

[0441]1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

[0442]1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

[0443]1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0444] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0445]2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

[0446]2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

[0447] 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

[0448] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0449] 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

[0450] 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

[0451]2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

[0452]2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

[0453] 2-aminobutane,

[0454] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0455]2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

[0456]2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0457] 2-phenylphenol (OPP),

[0458] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

[0459]3,5-dichloro-N-[cyano[(1-methyl-2-propinyl)-oxy]-methyl]-benzamide,

[0460] 3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

[0461] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0462]4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0463] 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

[0464]8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

[0465] 8-hydroxyquinoline sulphate,

[0466] 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

[0467]bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

[0468] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0469]cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

[0470] ethyl[(4-chlorophenyl)-azo]-cyanoacetate,

[0471] potassium hydrogencarbonate,

[0472] methanetetrathiol sodium salt,

[0473] methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0474] methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0475] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0476] N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

[0477]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0478]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0479] N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

[0480] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

[0481] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidineamine,

[0482]N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

[0483] N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

[0484] N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

[0485]N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

[0486] N-formyl-N-hydroxy-DL-alanine sodium salt,

[0487]O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0488] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0489] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0490] spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,

[0491] Bactericides:

[0492] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0493] Insecticides/acaricides/nematicides:

[0494] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

[0495]Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

[0496] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, cis-resmethrin, cispermethrin, clocythrin, cloethocarb,clofentezine, cyanophos, cycloprene, cycloprothrin, cyfluthrin,cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0497] deltamethrin, demeton M, demeton S, demeton-S-methyl,diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoat,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0498] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,etoxazole, etrimfos,

[0499] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

[0500] granulosis viruses,

[0501] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene,

[0502] imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

[0503] lambda-cyhalothrin, lufenuron,

[0504] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, monocrotophos,

[0505] naled, nitenpyram, nithiazine, novaluron, nuclear polyhedrosisviruses,

[0506] omethoat, oxamyl, oxydemethon M,

[0507]Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoat, phorat, phosalone, phosmet, phosphamidon, phoxim, pirimicarb,pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur, prothiofos,prothoat, pymetrozine, pyraclofos, pyresmethrin, pyrethrum, pyridaben,pyridathion, pyrimidifen, pyriproxyfen,

[0508] quinalphos,

[0509] ribavirin,

[0510] salithion, sebufos, silafluofen, spinosad, sulfotep, sulprofos,

[0511] tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

[0512] vamidothion, vaniliprole, Verticillium lecanii,

[0513] zeta-cypermethrin, zolaprofos,

[0514] (1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

[0515] (3-phenoxyphenyl)-methyl2,2,3,3-tetramethylcyclopropanecarboxylate,

[0516]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

[0517]2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

[0518] 2-(acetlyoxy)-3-dodecyl-1,4-naphthalenedione,

[0519]2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0520]2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0521] 3-methylphenyl propylcarbamate

[0522] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

[0523]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

[0524]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

[0525]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

[0526]Bacillus thuringiensis strain EG-2348,

[0527] [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

[0528]2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[0529][3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

[0530] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

[0531]ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

[0532] N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

[0533]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

[0534] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

[0535] N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

[0536] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

[0537]O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

[0538] Herbicides:

[0539] acetochlor, acifluorfen(-sodium), aclonifen, alachlor,alloxydim(-sodium), ametryne, amidochlor, amidosulflron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, benazolin(-ethyl),benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap,benzoylprop(-ethyl), bialaphos, bifenox, bispyribac(-sodium),bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate,cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl),chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim,clodinafop(-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron(-methyl), cloransulam(-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop(-butyl),2,4-D, 2,4-DB, 2,4-DP, desmedipham, diallate, dicamba,diclofop(-methyl), diclosulam, diethatyl(-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulfiron(-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), fentrazamide,flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl),flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate,flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl),flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone,fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl,-sodium), flurenol(-butyl), fluridone, fluroxypyr(-meptyl),flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen,glufosinate(-ammonium), glyphosate(-isopropylammonium), halosafen,haloxyfop(-ethoxyethyl), haloxyfop(-P-methyl), hexazinone,imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron,metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, piperophos, pretilachlor, primisulfuron(-methyl),prometryn, propachlor, propanil, propaquizafop, propisochlor,propyzamide, prosulfocarb, prosulfuron, pyraflufen(-ethyl), pyrazolate,pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-P-tefuryl),rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone,sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron,tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide,thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb,tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron(-methyl),triclopyr, tridiphane, trifluralin and triflusulfuron.

[0540] Furthermore, the active compound according to the invention, inits commercial formulations and in the use forms prepared from theseformulations, can be present as a mixture with synergists. Synergistsare compounds which increase the activity of the active compoundswithout it being necessary for the added synergist to be active itself.

[0541] The active compound content of the use forms prepared from thecommercial formulations can vary within wide ranges. The concentrationof active compound in the use forms can be from 0.0000001 to 95% byweight of active compound, preferably between 0.0001 and 1% by weight.

[0542] Application is carried out in a customary manner adapted to theuse forms.

[0543] The active compounds are furthermore suitable for controllinganimal pests, preferably arthropods and nematodes, in particular insectsand arachnids, which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienesector. They are active against normally sensitive and resistant speciesand against all or some stages of development. The abovementioned pestsinclude:

[0544] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0545] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0546] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spec.

[0547] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0548] From the order of the Thysanura, for example, Lepisma saccharina.

[0549] From the order of the Collembola, for example, Onychiurusarmatus.

[0550] From the order of the Blattaria or Orthoptera, for example,Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattellagermanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoriamigratorioides, Melanoplus differentialis and Schistocerca gregaria.

[0551] From the order of the Dermaptera, for example, Forficulaauricularia.

[0552] From the order of the Isoptera, for example, Reticulitermes spp.

[0553] From the order of the Anoplura, for example, Phylloxeravastatrix, Pemphigus spp.,

[0554]Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

[0555] From the order of the Mallophaga, for example, Trichodectes spp.and Damalinea spp.

[0556] From the order of the Thysanoptera, for example, Frankliniellaoccidentalis,

[0557]Hercinothrips femoralis, Thrips palmi and Thrips tabaci.

[0558] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0559] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vasturix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium comi, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp. and Psylla spp.

[0560] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Plutellaxylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.,Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoaspp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua,Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofinannophila pseudospretella,Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysiaambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp. andAulema oryzae.

[0561] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis, Costelytra zealandica and Lissorhoptus oryzophilus.

[0562] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0563] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Liriomyza spp., Stomoxys spp.,Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibiohortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitiscapitata, Dacus oleae, Tipula paludosa, Hylemnia spp. and Liviomyza spp.

[0564] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp.

[0565] From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

[0566] From the order of the Acarina, for example, Acarus siro, Argasspp., Omithodoros spp., Dermanyssus gallinae, Eriophyes ribis,Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommaspp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp.,Tetranychus spp., Hemitarsonemus spp. and Brevipulpus spp.

[0567] The phytoparasitic nematodes include, for example, Pratylenchusspp. Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heteroderma spp., Globodera spp., Meloidogyne spp.,Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.and Bursaphelenchus spp.

[0568] The active compounds according to the invention have highinsecticidal and acaricidal activity after foliar and soil application.

[0569] At certain concentrations or application rates, the compoundsaccording to the invention also have fungicidal action. Furthermore,they can also be used as microbicides or antimycotics.

[0570] When used against hygiene pests and pests of stored products, theactive compound has excellent residual activity on wood and clay, andgood stability to alkali on limed substrates.

[0571] The active compounds according to the invention act not onlyagainst plant, hygiene and stored-product pests, but also in theveterinary medicine sector against animal parasites (ectoparasites),such as hard ticks, soft ticks, mange mites, leaf mites, flies (bitingand licking), parasitic fly larvae, lice, hair lice, feather lice andfleas. These parasites include:

[0572] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0573] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

[0574] From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Caalliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0575] From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[0576] From the order of the Heteropterida, for example, Cimex spp.,Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[0577] From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

[0578] From the subclass of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[0579] From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0580] The active compounds of the formula (I) according to theinvention are also suitable for controlling arthropods which infestagricultural productive livestock, such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, caged birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, cases of death and reduction inproductivity (for meat, milk, wool, hides, eggs, honey etc.) should bediminished, so that more economic and easier animal husbandry ispossible by use of the active compounds according to the invention.

[0581] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

[0582] When used for cattle, poultry, pets and the like, the activecompounds of the formula (I) can be used as formulations (for examplepowders, emulsions, free-flowing compositions), which comprise theactive compounds in an amount of 1 to 80% by weight, directly or after100- to 10 000-fold dilution, or they can be used as a chemical bath.

[0583] It has furthermore been found that the compounds of the formula(I) according to the invention also have a strong insecticidal actionagainst insects which destroy industrial materials.

[0584] The following insects may be mentioned as examples and aspreferred—but without a limitation:

[0585] Beetles, such as Hylotrupes bajulus, Chlorophorus pilosis,Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis,Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus,Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec. and Dinoderus minutus.

[0586] Hymenopterons, such as Sirex juvencus, Urocerus gigas, Urocerusgigas taignus and Urocerus augur.

[0587] Termites, such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis and Coptotermes formosanus.

[0588] Bristletails, such as Lepisma saccarina.

[0589] Industrial materials in the present connection are to beunderstood as meaning non-living materials, such as, preferably,plastics, adhesives, sizes, papers and cardboards, leather, wood andprocessed wood products and coating compositions.

[0590] Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

[0591] Wood and processed wood products which can be protected by theagents according to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood panelling, woodenwindows and doors, plywood, chipboard, joinery or wooden products whichare used quite generally in house-building or in building joinery.

[0592] The active compounds can be used as such, in the form ofconcentrates or in generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[0593] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersing agent and/or binder or fixing agent,a water repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

[0594] The insecticidal compositions or concentrates used for theprotection of wood and timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

[0595] The amount of the compositions or concentrates employed dependson the nature and occurrence of the insects and on the medium. Theoptimum amount employed can be determined for the use in each case by aseries of tests. In general, however, it is sufficient to employ 0.0001to 20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be protected.

[0596] Solvents and/or diluents which are used are an organochemicalsolvent or solvent mixture and/or an oily or oil-like organochemicalsolvent or solvent mixture of low volatility and/or a polarorganochemical solvent or solvent mixture and/or water, and ifappropriate an emulsifier and/or wetting agent.

[0597] Organochemical solvents which are preferably used are oily oroil-like solvents having an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C. Substances which are used as suchoily or oil-like water-insoluble solvents of low volatility areappropriate mineral oils or aromatic fractions thereof, or solventmixtures containing mineral oils, preferably white spirit, petroleumand/or alkylbenzene.

[0598] Mineral oils having a boiling range from 170 to 220° C., whitespirit having a boiling range from 170 to 220° C., spindle oil having aboiling range from 250 to 350° C., petroleum and aromatics having aboiling range from 160 to 280° C., turpentine oil and the like, areadvantageously employed.

[0599] In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

[0600] The organic oily or oil-like solvents of low volatility whichhave an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., can be replaced in part by organochemicalsolvents of high or medium volatility, providing that the solventmixture likewise has an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

[0601] According to a preferred embodiment, some of the organochemicalsolvent or solvent mixture is replaced by an aliphatic polarorganochemical solvent or solvent mixture. Aliphatic organochemicalsolvents containing hydroxyl and/or ester and/or ether groups, such as,for example, glycol ethers, esters or the like, are preferably used.

[0602] Organochemical binders which are used in the context of thepresent invention are the synthetic resins and/or binding drying oilswhich are known per se, are water-dilutable and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders consisting of or comprising an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-cumarone resin, silicone resin, drying vegetable oils and/ordrying oils and/or physically drying binders based on a natural and/orsynthetic resin.

[0603] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances can also be used as binders in an amount of up to 10% byweight. Dyestuffs, pigments, water-repelling agents, odour correctantsand inhibitors or anticorrosive agents and the like which are known perse can additionally be employed.

[0604] It is preferred according to the invention for the composition orconcentrate to comprise, as the organochemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

[0605] All or some of the binder mentioned can be replaced by a fixingagent (mixture) or a plasticizer (mixture). These additives are intendedto prevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

[0606] The plasticizers originate from the chemical classes of phthalicacid esters, such as dibutyl, dioctyl or benzyl butyl phthalate,phosphoric acid esters, such as tributyl phosphate, adipic acid esters,such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate oramyl stearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

[0607] Fixing agents are based chemically on polyvinyl alkyl ethers,such as, for example, polyvinyl methyl ether or ketones, such asbenzophenone or ethylenebenzophenone.

[0608] Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersing agents.

[0609] Particularly effective preservation of wood is achieved byimpregnation processes on a large industrial scale, for example vacuum,double vacuum or pressure processes.

[0610] The ready-to-use compositions can also comprise otherinsecticides, if appropriate, and also one or more fungicides, ifappropriate.

[0611] Possible additional mixing components are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an explicit constituent of the presentapplication.

[0612] Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and also fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

[0613] The active compounds according to the invention can be usedparticularly effectively for controlling plant-damaging insects, suchas, for example, against the larvae of the mustard beetle (Phaedoncochleariae), against the larvae of the green rice leafhopper(Nephotettix cincticeps) and against the larvae of the green peach aphid(Myzus persicae).

[0614] In addition to the acaricidal, herbicidal and insecticidalproperties described, a fungicidal activity of the active compoundsaccording to the invention is noticeable. In both ‘in vitro’ and ‘invivo’ studies, a broad fungicidal effect can be observed.

[0615] Moreover, it was noticed that the active compounds are, inparticular, also suitable for controlling mildew, leaf blotch andFusaria on the infected plants.

[0616] The preparation and the use of the active compounds according tothe invention is shown in the examples below.

PREPARATION EXAMPLES Example 1

[0617]

[0618] (Process C)

[0619] At 60° C., a mixture of 0.9 g of 4-chlorobenzoylacetonitrile andtrimethyl formate is admixed with 0.3 g of isopropylamine. The reactionmixture is heated at 125-130° C., and the reaction is monitored bythin-layer chromatography.

[0620] After all of the starting material has been converted, thereaction mixture is concentrated using a rotary evaporator, and theproduct that has been formed is extracted using methylenechloride/NaHCO₃ solution.

[0621] The compounds contained in the solution were separated by columnchromatography on a silica gel phase using the mobile phase hexane/ethylacetate (2:1).

[0622] One of the main fractions gave, after evaporation of the solvent,0.65 g (yield 55% of theory) of2-(4-chlorobenzoyl)-3-(N-methylamino)-propenonitrile of melting point148° C.

Example 2

[0623]

[0624] (Process A)

[0625] A mixture of 0.7 g of 4-chloro-benzoylacetonitrile, 0.5 g ofmethyl N-methyliminoacetate and 8 ml of toluene is initially charged andheated at 80° C. The reaction mixture is stirred at 80° C. for 10 hoursand then concentrated by evaporating the solvent, and the precipitatedsolid is recrystallized from methyl t-butyl ether/di-chloromethane.

[0626] This gives 0.51 g (yield 54.9% of theory) of2-(4-chlorobenzoyl)-3-(N-methylamino)-crotononitrile of melting point152° C.

Example 3

[0627]

[0628] (Process A)

[0629] 1 g of thiomethyl N-methyl-4-chloroiminobenzoate and 1 g of4-chlorobenzoylacetonitrile are added to 10 ml of toluene. The mixtureis stirred for 4 hours. After complete conversion (TLC), the componentscontained in the mixture are separated by column chromatography on asilica gel phase using the mobile phase hexane/ethyl acetate (2:1).

[0630] One of the main fractions gave, after evaporation of the solvent,1.30 g (yield 81% of theory) of2-(4-chlorobenzoyl)-3-(4-chlorophenyl)-3-(N-methylamino)-propenonitrileof melting point 182° C.

Example 4

[0631]

[0632] At 0° C., 5 g of N-methyl-4-chloro-thiobenzamide are dissolved inacetonitrile and admixed with 3.3 g of potassium hydroxide. At atemperature of 20° C., 4 g of methyl iodide are added, and the mixtureis then heated at 60° C. After complete conversion (TLC), the reactionmixture is filtered and concentrated by evaporation of the solvent usinga rotary evaporator.

[0633] This gave 2.0 g (yield 40% of theory) of thiomethylN-methyl-4-chloroiminobenzoate, which decomposes readily.

Example 5

[0634]

[0635] At 0° C., 80 g of the compound N-methyl-4-chloro-benzamide in 600ml of pyridine are admixed with 107 g of phosphorus pentasulphide. Themixture is heated to 80° C. and then kept at this temperature for 2hours.

[0636] The components contained in the mixture were separated by columnchromatography on a silica gel phase using the mobile phase hexane/ethylacetate (10:1).

[0637] One of the main fractions gave, after evaporation of the solvent,46 g of N-methyl-4-chloro-thiobenzamide (yield 52% of theory).

Example 6

[0638]

[0639] At −30° C., about 200 ml of methylamine are condensed into 400 mlof THF. At from −10° C. to 0° C., the reaction solution is then admixedwith 75 g of 4-chlorobenzoyl chloride (as a solution in 30 ml of THF).At 20° C., the further progress of the reaction is monitored bythin-layer chromatography.

[0640] After complete conversion, the compounds contained in the mixtureare separated by column chromatography on a silica gel phase using themobile phase hexane/ethyl acetate (2:1).

[0641] The main fraction gave, after evaporation of the solvent, 80 g(yield 99% of theory) of N-methyl-4-chloro-benzamide.

Example 7

[0642]

[0643] 1 g of 4-chlorobenzoyl-acetamide (known from JP-A 89-108491) and10 ml of trimethyl orthoformate are mixed and reacted at 90° C. for onehour. After cooling to 60° C., 2 ml of i-propylamine are added. Themixture is then heated at 110° C. for 10 minutes. After completeconversion, the compounds contained in the mixture are separated bycolumn chromatography on a silica gel phase using the mobile phasehexane/ethyl acetate (2:1).

[0644] The main fraction gave, after evaporation of the solvent, 0.2 g(yield 7.5% of theory) of2-(4-chlorobenzoyl)-3-(N-isopropylamino)-propenamide.

[0645]¹H-NMR (400 MHz, d₆-DMSO): δ=1.14 (d, 6H, CH(CH₃ )₂), 3.58 (m, 1H,CH(CH₃)₂), 7.16 (d, br, 1H, CONH), 8.86 (d, br, 1H, CONH), 10.83 (br,1H, NH) ppm, UV (acetonitrile/H₃PO⁴ buffer gradient): λ_(max) 244, 292nm.

Example 8

[0646]

[0647] (Process D)

[0648] At a temperature of 20° C., 0.8 g of2-(4-chlorobenzoyl)-3-(N-cyclopropylamino)-crotononitrile is admixedwith 0.7 g of Lawesson's reagent and reacted for one hour. Aftercomplete conversion, the components contained in the mixture areseparated by column chromatography on a silica gel phase using themobile phase hexane/ethyl acetate (2:1).

[0649] The main fraction gave, after evaporation of the solvent, 0.7 g(yield 84% of theory) of2-[(4-chlorophenyl)-thiocarbonyl]-3-(N-cyclopropylamino)-crotononitrileof melting point 215° C.

Example 9

[0650]

[0651] 30.0 g of 6-fluoro-4H-benz[1,4]oxazin-3-one are initially chargedin 300 ml of dichloromethane, and 37.4 g of bromine are then slowlyadded dropwise at room temperature. The mixture is heated at 30° C. withstirring for 15 h. The reaction solution is cooled to room temperatureand poured onto ice. The aqueous phase is extracted repeatedly withdichloromethane. The combined organic phases are washed with saturatedsodium thiosulphate solution, dried over magnesium sulphate andconcentrated. This give 44.1 g (yield 99.5% of theory) of7-bromo-6-fluoro-4H-benz[1,4]oxazin-3-one of melting point 244° C.

Example 10

[0652]

[0653] Under argon, 25.5 g of 7-bromo-6-fluoro-4H-benz[1,4]oxazin-3-oneare initially charged in 120 ml of DMF and, at 0° C., admixed a littleat a time with 28.0 g of potassium carbonate. At 0° C., 13.0 ml of allylbromide are then added dropwise, and the mixture is stirred at roomtemperature for 15 h. The mixture is poured into 1200 ml of ice-waterand extracted repeatedly with ethyl acetate, and the combined organicphases are washed with saturated aqueous sodium chloride solution, driedover magnesium sulphate and concentrated.

[0654] The crude product is purified by silica gel column chromatography(mobile phase: ethyl acetate/cyclohexane 1:1), giving 23.8 g (yield81.9% of theory) of N-allyl-7-bromo-6-fluoro-4H-benz[1,4]oxazin-3-one ofmelting point 92° C.

Example 11

[0655]

[0656] 20.0 g of N-benzyl-7-methoxycarbonyl-4H-benz[1,4]oxazin-3-one areinitially charged in 750 ml of MeOH. At room temperature, 35 ml of 2Naqueous sodium hydroxide solution are added dropwise, and the mixture isstirred at 40-55° C. for 30 h. The reaction solution is cooled to roomtemperature and poured into a mixture of 200 ml of 1N HCl and 1 kg ofice. The crude product is filtered off with suction, washed with waterand dried. This gives 18.2 g (yield 95.5% of theory) ofN-benzyl-7-hydroxycarbonyl-4H-benz[1,4]oxazin-3-one of melting point230° C.

[0657] The following compounds are obtained analogously to thepreparation examples and in accordance with the general statements onthe preparation of compounds of the formula (I): TABLE 1 Comp. No. G_(n)Y Z m.p. ° C. I-a-1 4-Cl i-C₃H₇ H 148 I-a-2 4-Cl

H 119 I-a-3 3,5-(CF₃)₂ C₂H₅ H 78-80 I-a-4 3,5-(CF₃)₂ CH₃ H 150 I-a-53,5-(CF₃)₂ H H 149 I-a-7 4-Cl CH₃ H 208 I-a-8 4-Cl

H 138 I-a-9 3,5-(CF₃)₂ H 110 I-a-10 4-Cl F₃C—CH₂— H 155 I-a-113,5-(CF₃)₂ F₃C—CH₂— H 154 I-a-12 3,5-(CF₃)₂ i-C₃H₇ H 134 I-a-13 4-Cl

CH₃ 58-60 I-a-14 4-Cl i-C₃H₇ CH₃ 137 I-a-15 3,5-(CF₃)₂ i-C₃H₇ CH₃118-120 I-a-16 3,5-(CF₃)₂ C₂H₅ CH₃ oil I-a-17 3,5-(CF₃)₂ CH₃ CH₃ oilI-a-18 3,5-(CF₃)₂ H CH₃ 172-174 I-a-19 4-Cl H CH₃ 162 I-a-20 4-Cl CH₃CH₃ 171 I-a-21 4-Cl F₃C—CH₂ CH₃ 145 I-a-22 3,5-(CF₃)₂ F₃C—CH₂ CH₃ 122I-a-23 4-Cl

CH₃ 82-84 I-a-24 3,5-(CF₃)₂

CH₃ 78-80 I-a-25 4-Cl i-C₃H₇ C₂H₅ 162 I-a-26 3,5-(CF₃)₂ C₂H₅ C₂H₅ 105I-a-27 4-Cl CH₃ C₂H₅ 149 I-a-28 3,5-(CF₃)₂ i-C₃H₇ n-C₃H₇  83 I-a-29 4-Cli-C₃H₇ n-C₃H₇ 102 I-a-30 3,5-(CF₃)₂ CH₃ n-C₃H₇ oil I-a-31 3,5-(CF₃)₂C₂H₅ n-C₃H₇ oil I-a-32 3,5-(CF₃)₂ i-C₃H₇ n-C₄H₉  73 I-a-33 3,5-(CF₃)₂C₂H₅ n-C₄H₉ oil I-a-34 3,5-(CF₃)₂ CH₃ n-C₄H₉ oil I-a-35 4-Cl i-C₃H₇n-C₄H₉  60 I-a-36 4-Cl H

270 I-a-37 4-Cl H

242 I-a-38 4-Cl i-C₃H₇

144 I-a-39 3,5-(CF₃)₂ H

146 I-a-40 3,5-(CF₃)₂ H

182 I-a-42 3,5-(CF₃)₂ CH₃

170 I-a-43 4-Cl i-C₃H₇

150 I-a-44 4-Cl i-C₃H₇

146-148 I-a-45 4-Cl C₂H₅

135 I-a-46 3,5-(CF₃)₂ C₂H₅

132-134 I-a-47 3,5-(CF₃)₂ i-C₃H₇

138-140 I-a-48 3,5-(CF₃)₂ i-C₃H₇

152 I-a-49 3,5-(CF₃)₂ C₂H₅

182 I-a-50 3,5-(CF₃)₂ CH₃

173 I-a-51 3,5-(CF₃)₂ C₂H₅

147 I-a-52 3,5-(CF₃)₂ CH₃

139 I-a-53 4-Cl C₂H₅

133 I-a-54 3,5-(CF₃)₂ i-C₃H₇

136-138 I-a-55 3,5-(CF₃)₂ C₂H₅

138 I-a-56 3,5-(CF₃)₂ CH₃

148 I-a-57 4-Cl i-C₃H₇

oil I-a-58 2,4-F₂ CH₃ CH₃ 146 I-a-59 4-Cl CH₃ CH₃ 152 I-a-60 4-Cl i-C₃H₇H I-a-61 3,5-(CF₃)₂ CH(CH₃)₂ C₂H₅ 123 I-a-62 4-Cl CH(CH₃)₂

oil I-a-63 4-Cl

CH₃ 113 I-a-64 2-F, 4-Cl, 5- O-allyl

CH₃  83 I-a-65 4-Cl

CH₃ 124 I-a-66 4-Cl n-C₃H₇ CH₃ 134 I-a-67 4-Cl CH₂CH(CH₃)₂ CH₃ 120I-a-68 4-Cl C(CH₃)₃ CH₃ 123 I-a-69 4-Cl CH₂C(CH₃)₃ CH₃ 147 I-a-70 4-Cl

CH₃ oil I-a-71 4-Cl

CH₃ oil I-a-72 4-Cl

CH₃ 134 I-a-73 3,5-(CF₃)₂ CH₂CH(CH₃)C₂H₅ CH₃ oil I-a-74 4-Cl cyclo-C₅H₉CH₃  98 I-a-75 4-Cl CH₂CH(CH₃)C₂H₅ CH₃ oil I-a-76 4-Cl C(CH₃)₂CH₂C(CH₃)₃CH₃  99 I-a-77 4-Cl C(CH₃)₂(CN) CH₃ 143 I-a-78 4-Cl C(C₂H₅)₂C≡CH CH₃ oilI-a-79 4-Cl C(CH₃)₂C≡CH CH₃  95 I-a-80 4-Cl C(CH₃)₂C₂H₅ CH₃ oil I-a-814-Cl

H 124 I-a-82 3,5-(CF₃)₂ CH₂CH═CH₂ H  99 I-a-83 2-F, 4-Cl, CH(CH₃)₂ H oil5-O-allyl I-a-84 2-F, 4-Cl, 5-O-allyl

H 143 I-a-85 2-F, 4-Cl, CH₃ H 162 5-O-allyl I-a-86 2-F, 4-CN, CH₃ H 1585-O-benzyl I-a-87 4-Cl

H 133 I-a-88 4-Cl n-C₃H₇ H 108 I-a-89 4-Cl CH₂CH(CH₃)₂ H 123 I-a-90 4-ClC(CH₃)₃ H 125 I-a-91 4-Cl CH₂C(CH₃)₃ H 121 I-a-92 4-Cl

H oil I-a-93 4-Cl

H oil I-a-94 3,5-(CF₃)₂ CH(CH₃)C₂H₅ H 146 I-a-95 4-Cl C(CH₃)₂CH₂OH CH₃oil I-a-96 4-Cl C(CH₃)₂CH(CH₃) CH₃ 181 CH₂OH I-a-97 4-Cl C(C₃H₆OH)₃ CH₃oil I-a-98 4-Cl

CH₃ oil I-a-99 4-Cl

CH₃ oil I-a-100 4-Cl

CH₃ oil I-a-101 4-Cl

CH₃ wax I-a-102 4-Cl

CH₃ wax I-a-103 4-Cl

CH₃ 191 I-a-104 4-Cl

CH₃ wax I-a-105 4-Cl

CH₃ oil I-a-106 4-Cl

CH₃ oil I-a-107 4-Cl

CH₃ 105 I-a-108 4-Cl

CH₃ oil I-a-109 4-Cl

CH₃ oil I-a-110 4-Cl

CH₃ 199 I-a-111 4-Cl

CH₃ 121 I-a-112 4-Cl

CH₃ 193 I-a-113 4-Cl

CH₃ oil I-a-114 4-Cl

CH₃ oil I-a-115 4-Cl

CH₃ 119 I-a-116 4-Cl

CH₃ wax I-a-117 4-Cl

CH₃ oil I-a-118 4-Cl

CH₃ oil I-a-119 4-Cl

CH₃ oil I-a-120 4-Cl

CH₃ wax I-a-121 4-Cl

CH₃ 146 I-a-122 4-Cl

CH₃  99 I-a-123 4-Cl

CH₃ oil I-a-124 4-Cl

CH₃ oil I-a-125 4-Cl C(CH₃)(CH₂F)₂ CH₃ 114 I-a-126 4-Cl C(CH₃)₂CH₂F CH₃106 I-a-127 4-Cl C(CH₃)₂CF₃ CH₃ wax I-a-128 4-Cl C(CH₂F)₃ CH₃ oilI-a-129 4-Cl C(CHF₂)₃ CH₃ oil I-a-130 4-Cl

CH₃ 101 I-a-131 4-Cl

CH₃ oil I-a-132 4-Cl

CH₃ wax I-a-133 4-Cl

CH₃ oil I-a-134 2-F, 4-Cl, 5- C(CH₃)₃ CH₃ 119 O-allyl I-a-135 3,5-(CF₃)₂CH₃

oil I-a-136 4-Cl

CH₃ 140 I-a-137 4-Cl

CH₃ 115 I-a-138 4-Cl

CH₃ oil I-a-139 4-Cl

CH₃ oil I-a-140 4-Cl

CH₃ oil I-a-141 3,5-(CF₃)₂

CH₃ oil I-a-142 3,5-(CF₃)₂ CH₂CH(CH₃)₂ CH₃ oil I-a-143 3,5-(CF₃)₂C(CH₃)₃ CH₃ oil I-a-144 3,5-(CF₃)₂ CH₂C(CH₃)₃ CH₃ oil I-a-145 3,5-(CF₃)₂

CH₃ oil I-a-146 3,5-(CF₃)₂

CH₃ oil I-a-147 3,5-(CF₃)₂

CH₃ oil I-a-148 3,5-(CF₃)₂

CH₃ oil I-a-149 3,5-(CF₃)₂

CH₃ oil I-a-150 3,5-(CF₃)₂

CH₃ oil I-a-151 3,5-(CF₃)₂ cyclo-C₅H₉ CH₃ oil I-a-152 3,5-(CF₃)₂ n-C₃H₇CH₃ oil I-a-153 3,5-(CF₃)₂

CH₃ oil I-a-154 4-Cl

H 131 I-a-155 4-Cl

H oil I-a-156 4-Cl

H I-a-157 4-Cl CH₂CH(CH₃)C₂H₅ H  84 I-a-158 3,5-(CF₃)₂

H 131 I-a-159 3,5-(CF₃)₂ cyclo-C₆H₁₁ H 158 I-a-160 3,5-(CF₃)₂

H 124 I-a-161 3,5-(CF₃)₂

H 149 I-a-162 3,5-(CF₃)₂ n-C₃H₇ H 119 I-a-163 3,5-(CF₃)₂ CH₂CH(CH₃)₂ H144 I-a-164 3,5-(CF₃)₂ C(CH₃)₃ H 123 I-a-165 3,5-(CF₃)₂ CH₂C(CH₃)₃ H 139I-a-166 3,5-(CF₃)₂

H oil I-a-167 3,5-(CF₃)₂

H oil I-a-168 3,5-(CF₃)₂

H  95 I-a-169 3,5-(CF₃)₂

H 102 I-a-170 3,5-(CF₃)₂

H oil I-a-171 3,5-(CF₃)₂

H 134 I-a-172 3,5-(CF₃)₂ CH₂CH(CH₃)C₂H₅ H 119

[0658] The following compound is obtained analogously to the preparationexamples and in accordance with the general statements on thepreparation of compounds of formula (I) in the description: TABLE 2(I-b)

Comp. No. Y Z m.p. ° C. I-b-1 C(CH₃)₃ CH₃ oil

[0659] The following compounds are obtained analogously to PreparationExample 4 and in accordance with the general statements on thepreparation of compounds of the formula (III): (III-a)

Comp. N. R⁸ Y Rg m.p. ° C. III-a-1 CH₃ CH₃ 4-Cl oil III-a-2 CH₃ allyl Hoil III-a-3 CH₃ allyl 4-Cl oil III-a-4 CH₃ i-C₃H₇ 4-Cl oil III-a-5 CH₃C₂H₅ 4-Cl oil III-a-6 CH₃ CH₂—CF₃ 4-Cl oil

[0660] The following compounds are obtained analogously to PreparationExample 5 and in accordance with the general statements on thepreparation of compounds of the formula (VI): (VI-a-1)

Comp. No. Y Rg VI-a-1 CH₃ 4-Cl VI-a-2 i-C₃H₇ 4-Cl VI-a-3 allyl 4-ClVI-a-4 C₂H₅ 4-Cl VI-a-5 CH₂—CF₃ 4-Cl

Example

[0661] Post-Emergence Test Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0662] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0663] Test plants of a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. After 3 weeks, thedegree of damage to the plants is rated in % damage in comparison to thedevelopment of the untreated control.

[0664] The figures denote:  0% = no effect (like untreated control) 100%= total destruction

[0665] In this test, for example, the compounds of Preparation ExamplesI-a-35, I-a-20, I-a-4, I-a-17, I-a-3, I-a-59, I-a-58, I-a-29, I-a-8 andI-a-23 exhibit strong activity against weeds, and some are toleratedwell by crop plants, such as, for example, wheat.

Example

[0666] Pre-Emergence Test Solvent: 5 parts by weight of acetoneEmulsifier: 1 part by weight of alkylaryl polyglycol ether

[0667] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0668] Seeds of the test plants are sown in normal soil and, after 24hours, watered with the preparation of active compound. The amount ofwater per unit area is advantageously kept constant. The concentrationof active compound in the preparation is immaterial, only theapplication rate of active compound per unit area matters. After threeweeks, the degree of damage to the plants is rated in % damage incomparison to the development of the untreated control.

[0669] The figures denote:  0% = no effect (like untreated control) 100%= total destruction

[0670] In this test, for example, the compounds of Preparation ExamplesI-a-3, I-a-17, I-a-20, I-a-4, I-a-58, I-a-59, I-a-23, I-a-8 and I-a-21exhibit strong activity against weeds, and some are tolerated well bycrop plants, such as, for example, wheat and soya.

Example A

[0671] Meloidogyne Test Solvent: 30 parts by weight of dimethylformamideEmulsifier:  1 part by weight of alkylaryl polyglycol ether

[0672] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0673] Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

[0674] After the desired period of time, the nematicidal action isdetermined in % using gall formation as a measure. 100% means that nogalls were found; 0% means that the number of galls on the treatedplants corresponds to that on the untreated control.

[0675] In this test, for example, the following compounds of thepreparation examples exhibit good activity: I-a-39, I-a-42, I-a-5

Example B

[0676] Phaedon Larvae Test Solvent: 30 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

[0677] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0678] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with larvae of the mustard beetle (Phaedon cochleariae)while the leaves are still moist.

[0679] After the desired period of time, the kill in % is determined.100% means that all beetle larvae have been killed; 0% means that noneof the beetle larvae have been killed.

[0680] In this test, for example, the following compounds of thepreparation examples show good activity: I-a-13, I-a-49, I-a-44, I-a-15,I-a-19, I-a-53

Example C

[0681] Plutella Test Solvent: 30 parts by weight of dimethylformamideEmulsifier:  1 part by weight of alkylaryl polyglycol ether

[0682] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0683] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the owlet moth (Plutella xylostella)while the leaves are still moist.

[0684] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0685] in this test, for example, the following compounds of thepreparation examples show good activity: I-a-58, I-a-45

Example D

[0686]Spodoptera frugiperda Test Solvent: 30 parts by weight ofdimethylformamide Emulsifier:  1 part by weight of alkylaryl polyglycolether

[0687] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0688] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the armyworm (Spodoptera frugiperda)while the leaves are still moist.

[0689] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0690] In this test, for example, the following compounds of thepreparation examples show good activity: I-a-42, I-a-45, I-a-48, I-a-18,I-a-52

Example E

[0691] Tetranychus Test (OP-Resistant/Dip Treatment) Solvent: 7 parts byweight of dimethylformamide Emulsifier: 1 part by weight of alkylarylpolyglycol ether

[0692] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0693] Bean plants (Phaseolus vulgaris) which are heavily infested byall stages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

[0694] After the desired period of time, the effect in % is determined.100% means that all spider mites have been killed; 0% means that none ofthe spider mites have been killed.

[0695] In this test, for example, the following compounds of thepreparation examples show good activity: I-a-3

1. Compounds of the general formula (I)

in which K represents oxygen or sulphur, Ar represents in each caseoptionally substituted phenyl, naphthyl, represents in each caseoptionally substituted mono- or bicyclic hetaryl having 5 to 10 ringatoms, or represents the group

 where B¹ represents hydrogen or halogen, two adjacent radicals—B² andB³ or B³ and B⁴—together represent one of the groupings below —Q¹—CQ²—,—Q¹—CQ²—Q³—, —Q¹—C(B⁶,B⁷)—Q³—, —C(B⁶,B⁷)—CQ²—, —C(B⁶,B⁷)—Q¹—CQ²—,—Q¹—C(B⁶,B⁷)—C(B⁶,B⁷)—, —Q¹—C(B⁶,B⁷)—C(B⁶,B⁷)—Q³—,—C(B⁶,B⁷)—C(B⁶,B⁷)—CQ²—, —Q¹—C(B⁶)═C(B⁶)—, —C(B⁶)═C(B⁶)—CQ²—,—Q¹—C(B⁶,B⁷)—CQ²—, —N(B⁸)—C(B⁶,B⁷)—CQ²—, —C(B⁶)═N—, —Q¹—CQ²—C(B⁶,B⁷)—,—Q¹—CQ²—N(B⁸)—, —Q¹—C(B⁶,B⁷)—CQ₂—N(B⁸)—, —C(B⁶,B⁷)—Q¹—CQ²—N(B⁸)—,—C(B⁶,B⁷)—C(B⁶,B⁷)—N(B⁸)—, —C(B⁶,B₇)—C(B₆,B⁷)—CQ²—N(B⁸)—,—C(B⁶)═C(B⁶)—N(B⁸)—, —C(B⁶)═C(B⁶)—CQ²—N(B⁸)—, —C(B⁶B⁷)—CQ²—N(B⁸)—,—N(B⁸)—C(B⁶,B⁷)—CQ²—N(B⁸)—, —C(B⁶)═N—N(B⁸)—, —Q¹—CQ²—C(B⁶,B⁷)—N(B⁸)—,—Q¹—C(B⁶,B⁷)—C(B⁶,B⁷)—CQ²—N(B⁸)—, —N(B⁸)—CQ²—C(B⁶)═N—,—Q¹—C(B⁶)═C(B⁶)—Q³—, —N(B⁸)—C(B⁶)═C(B⁶)—CQ²—, —N(B⁸)—C(B⁶)═N—,—N(B⁸)—C(B⁶,B⁷)—C(B⁶,B⁷)—Q³—, —N(B⁸)—CQ²—C(B⁶,B⁷)—Q⁴—,—N(B⁸)—CQ²—CQ²—Q³—, —Q¹—C(B⁶)═C(B⁶)—C(B⁶,B⁷)—, —Q¹—C(B⁶)═C(B⁶)—, and thefourth radical, B⁴ or B², represents hydrogen, thiocarbamoyl, cyano orhalogen, where Q¹, Q² and Q³ are identical or different and eachrepresent oxygen or sulphur, and Q⁴ represents —SO— or —SO₂—, B⁶ and B⁷are identical or different and individually represent hydrogen, halogenor alkyl or together represent alkanediyl, and B⁸ represents hydrogen,hydroxyl, represents in each case optionally cyano-, halogen-, alkoxy-,alkylcarbonyl- or alkoxy-carbonyl-substituted alkyl, alkylcarbonyl,alkoxycarbonyl, alkylthio or alkylsulphonyl, represents in each caseoptionally halogen-substituted alkenyl or alkinyl, represents in eachcase optionally halogen- or alkyl-substituted cycloalkyl orcyclo-alkylalkyl, represents in each case optionally halogen-substitutedalkoxy or alkenyloxy, represents in each case optionally cyano-,halogen-, alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substitutedarylalkyl or arylalkoxy, X represents CN,

Y represents hydrogen, represents in each case optionally substitutedalkyl, alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl, represents in eachcase optionally substituted cycloalkyl, cycloalkylalkyl which in eachcase optionally are interrupted in the cycle by heteroatoms, orrepresents in each case optionally substituted phenylalkyl orhetaryl-alkyl, Z represents hydrogen, represents in each case optionallysubstituted alkyl, phenyl or phenylalkyl, R¹ represents hydrogen,represents in each case optionally substituted saturated or unsaturatedalkyl or cycloalkyl, each of which is optionally interrupted byheteroatoms, represents in each case optionally substituted phenyl orhetaryl, represents in each case optionally substituted phenylalkyl orhetarylalkyl, and R² represents hydrogen, represents in each caseoptionally substituted saturated or unsaturated alkyl or alkoxy,represents in each case optionally substituted phenyl, phenylalkyl orphenylalkyloxy, or R¹, R² furthermore together with the nitrogen atom towhich they are attached represent an optionally substituted cycle whichis optionally substituted by one or more heteroatoms.
 2. Compoundsaccording to claim 1, characterized in that Ar represents Ar¹, where Ar¹represents phenyl, naphthyl or mono- or bicyclic hetaryl having five toten ring atoms, each of which radicals is optionally mono- topentasubstituted by halogen, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkinyl,C₁-C₈-alkoxy, C₂-C₈-alkenyloxy, C₃-C₈-alkinyloxy, C₁-C₈-alkylthio,C₁-C₆-alkylsulphonyl, C₁-C₆-halogenoalkyl, C₁-C₆-halogenoalkoxy,C₂-C₈-halogenoalkenyloxy, C₁-C₂-alkylidenediyl-dioxy,C₁-C₂-halogenalkylidenediyl-dioxy, halogeno-C₁-C₄-alkylthio,halogeno-C₁-C₄-alkylsulphonyl, phenyl-C₁-C₄-alkoxy, hydroxyl, mercapto,nitro, cyano, amino or by the groups

or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, naphthyl, five- or six-membered hetaryl,phenyl-C₁-C₄-alkyl, phenoxy, phenyl-S(O)_(g)—, five- or six-memberedhetaryloxy or hetaryl-S(O)_(g), where these substituents for their partare in each case optionally mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,nitro or cyano, where g represents 0, 1 or 2, or represents the group

 where B¹ represents hydrogen or halogen,  two adjacent radicals—B² andB³ or B³ and B⁴—together represent one of the groupings below—Q¹—CQ²—N(B⁸)—, —Q¹—C(B⁶,B⁷)—CQ²—N(B⁸)—, —N(B⁸)—C(B⁶,B⁷)—CQ²—N(B⁸)—,—Q¹—CQ²—C(B⁶,B⁷)—N(B⁸)—, —Q¹—C(B⁶)═C(B⁶)—C(B⁶,B⁷)—, —Q¹—C(B⁶)═C(B⁶)—,—N(B⁸)—CQ²—C(B⁶)═N— where Q¹ and Q² are identical or different and eachrepresent oxygen or sulphur, B⁶ and B⁷ are identical or different andindividually represent hydrogen or methyl, B⁸ represents hydrogen,hydroxyl, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, acetyl-, propionyl-, methoxycarbonyl- orethoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, represents in each case optionally fluorine- and/orchlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-, i- ors-butoxy, propenyloxy or butenyloxy, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methyl-, ethyl-,trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted benzyl or benzyloxy, and the fourthradical, B4 or B2, represents hydrogen, cyano, fluorine or chlorine, Krepresents oxygen or sulphur, L represents oxygen or sulphur, Xrepresents CN,

Y represents hydrogen, in each case optionally mono- orpoly-hydroxy-substituted C₁-C₁₂-alkyl, C₃-C₁₀-alkenyl, C₃-C₁₀-alkinyl,C₁-C₆-alkoxy-C₂-C₄-alkyl, di-C₁-C₆-alkoxy-C₂-C₄-alkyl,C₁-C₆-alkoxy-C₂-C₄-cyanoalkyl, C₁-C₆-alkylthio-C₂-C₄-alkyl,C₁-C₈-halogenoalkyl, C₁-C₈-halogenoalkenyl or C₁-C₈-cyanoalkyl,represents in each case optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, cyano-, halogenophenyl-, benzyl-,C₁-C₆-hydroxyalkyl- or halogen-substituted C₃-C₈-cycloalkyl orC₃-C₈-cycloalkyl-C₁-C₄-alkyl which are optionally interrupted in thecycle by oxygen, sulphur or nitrogen, represents phenyl-C₁-C₄-alkyl orfive- or six-membered hetaryl-C₁-C₄-alkyl, each of which is optionallymono- to tetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, Z representshydrogen, C₁-C₆-alkyl, represents phenyl or phenyl-C₁-C₄-alkyl, each ofwhich is optionally mono- to trisubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogeno-alkoxy, nitro orcyano, R¹ represents hydrogen, represents in each case optionallyfluorine-and/or chlorine-substituted C₁-C₁₀-alkyl, C₃-C₁₀-alkenyl,C₃-C₆-alkinyl, represents in each case optionally fluorine-, chlorine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl in which optionally one methylene group may bereplaced by oxygen or sulphur, or represents phenyl, pyridyl, thienyl,pyrimidyl, thiazolyl, phenyl-C₁-C₄-alkyl, pyridyl-C₁-C₂-alkyl,thiazolyl-C₁-C₂-alkyl, each of which is optionally mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, R² representshydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl, or R¹, R² furthermore togetherwith the nitrogen atom to which they are attached represent an in eachcase optionally C₁-C₄-alkyl-substituted five- to eight-membered cycle inwhich optionally one methylene group may be replaced by oxygen orsulphur, R³ represents in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₃-C₁₀-alkinyl,C₁-C₁₀-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, ineach case optionally fluorine-, chlorine-, C₁-C₄-alkyl- and/orC₁-C₄-alkoxy-substituted C₃-C₈-cyeloalkyl or C₃-C₈-cycloalkoxy in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenoxy, benzyloxy, five- or six-membered hetaryl orphenyl-C₁-C₄-alkyl, each of which may optionally be mono- totetrasubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro, or, in thecase of the radicals a), c) and f) mentioned under Ar, also represents agroup

R⁴ represents hydrogen or C₁-C₄-alkyl, R⁵ represents hydrogen oroptionally fluorine- and/or chlorine-substituted C₁-C₄-alkyl, R⁶represents hydrogen, in each case optionally fluorine- and/orchlorine-substituted C₁-C₁₀-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₁₀-alkoxy, C₃-C₈-alkenyloxy, optionally fluorine-, chlorine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in whichoptionally one methylene group may be replaced by oxygen or sulphur,represents phenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₂-alkoxy, each ofwhich may optionally be mono- to tetrasubstituted by halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,cyano or nitro, R⁷ represents hydrogen, C₁-C₆-alkyl or C₃-C₆-alkenyl, orR⁶, R⁷ furthermore together with the nitrogen atom to which they areattached represent an optionally C₁-C₄-alkyl-substituted five- toeight-membered cycle in which optionally one methylene group may bereplaced by oxygen or sulphur.
 3. Compounds according to claim 1,characterized in that K represents oxygen or sulphur, Ar represents Ar¹,where Ar¹ represents phenyl, naphthyl, quinolinyl, thienyl, pyrimidyl,furanyl, thiazolyl, benzothiazolyl, oxazolyl, pyrazolyl or pyridyl, eachof which is optionally mono- to trisubstituted by fluorine, chlorine,bromine, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy,C₃-C₆-alkenyloxy, C₃-C₆-alkinyloxy, C₁-C₆-alkylthio,C₁-C₄-alkylsulphonyl, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy,C₂-C₄-halogenoalkenyloxy, C₁-C₂-alkylidenediyl-dioxy,C₁-C₂-halogenoalkylidenediyl-dioxy, halogeno-C₁-C₂-alkylthio,halogeno-C₁-C₂-alkylsulphonyl, phenyl-C₁-C₄-alkoxy, hydroxyl, mercapto,nitro, cyano, amino or by one of the groups below

or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, pyrimidyl, thienyl, furanyl, thiazolyl,tetrazolyl, triazolyl, benzyl, phenoxy, phenyl-S(O)_(g)—, pyridyloxy,pyrimidyloxy, thiazolyloxy, pyridyl-S(O)_(g)—, pyrimidyl-S(O)_(g)— orthiazolyl-S(O)_(g)—, where these substituents for their part areoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₂-C₄-alkenyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, where g represents0, 1 or 2, orrepresents the group

 where B¹ represents hydrogen or halogen,  two adjacent radicals—B² andB³ or B³ and B⁴—together represent the grouping below—Q¹—C(B⁶,B⁷)—CQ²—N(B⁸)—, where Q¹ and Q² are identical or different andeach represent oxygen or sulphur, B⁶ and B⁷ are identical or differentand individually represent hydrogen or methyl, B8 represents hydrogen,hydroxyl, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, acetyl-, propionyl-, methoxycarbonyl- orethoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally fluorine-, chlorine- orbromine-substituted propenyl, butenyl, propinyl or butinyl, representsin each case optionally fluorine-, chlorine-, bromine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, represents in each case optionally fluorine- and/orchlorine-substituted methoxy, ethoxy, n- or i-propoxy, n-, i- ors-butoxy, propenyloxy or butenyloxy, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methyl, ethyl-,trifluoromethyl-, methoxy-, ethoxy-, difluoromethoxy- ortrifluoromethoxy-substituted benzyl or benzyloxy, and the fourthradical, B⁴ or B², represents hydrogen, cyano, fluorine or chlorine, Yrepresents hydrogen, represents in each case optionally mono- orpoly-hydroxy-substituted C₁-C₁₀-alkyl, C₁-C₆-halogenoalkyl,C₃-C₈-alkenyl, C₃-C₈-alkinyl, C₁-C₄-alkoxy-C₂-C₃-alkyl,di-C₁-C₄-alkoxy-C₂-C₄-alkyl, C₁-C₄-alkoxy-C₂-C₄-cyanoalkyl,C₁-C₄-alkylthio-C₂-C₃-alkyl, C₁-C₆-halogenoalkenyl or C₁-C₆-cyanoalkyl,represents in each case optionally C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogeno-alkyl-, cyano-, halogenophenyl-, benzyl-,C₁-C₄-hydroxyalkyl-, fluorine- or chlorine-substituted C₃-C₆-cycloalkylor C₃-C₆-cycloalkyl-C₁-C₂-alkyl in which optionally one methylene groupmay be replaced by oxygen or nitrogen, represents phenyl-C₁-C₃-alkyl,thiazolylmethyl, triazolylmethyl or pyridylmethyl, each of which isoptionally mono- to trisubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano or nitro, Z represents hydrogen, C₁-C₃-alkyl, represents phenyl orbenzyl, each of which is optionally mono- or disubstituted by fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, nitro or cyano, R¹ represents hydrogen, representsin each case optionally fluorine and/or chlorine-substitutedC₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₄-alkinyl, represents optionallyfluorine-, chlorine-, C₁-C₂-alkyl-, C₁-C₂-alkoxy-substitutedC₃-C₆-cycloalkyl or represents phenyl or benzyl, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,cyano or nitro, R² represents hydrogen, represents C₁-C₄-alkyl orC₃-C₄-alkenyl, each of which is optionally substituted by fluorineand/or chlorine, or R¹, R² furthermore together with the nitrogen atomto which they are attached represent an optionally methyl-substitutedfive- or six-membered cycle in which optionally one methylene group maybe replaced by oxygen, R³ represents in each case optionally fluorine-and/or chlorine-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl, C₃-C₆-alkinyl,C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl, ineach case optionally fluorine-, chlorine-, C₁-C₂-alkyl- and/orC₁-C₂-alkoxy-substituted C₃-C₆-cycloalkyl or C₃-C₆-cycloalkoxy in whichoptionally one methylene group may be replaced by oxygen, representsphenyl, phenoxy, benzyloxy, thienyl, furanyl, pyridyl, pyrimidyl,thiazolyl, pyrazolyl or phenyl-C₁-C₂-alkyl, each of which is optionallymono- or disubstituted by fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₄-alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyanoor nitro, or, in the case of the radicals a), c) and f) mentioned underAr, also represents a group

R⁴ represents hydrogen, R⁵ represents hydrogen, methyl or ethyl, R⁶represents hydrogen, in each case optionally fluorine- and/orchlorine-substituted C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkinyl,C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, in which optionally one methylene groupmay be replaced by oxygen, represents phenyl or phenyl-C₁-C₂-alkyl, eachof which is optionally mono- or disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl, difluoro-methoxy,trifluoromethoxy, cyano or nitro, R⁷ represents hydrogen or C₁-C₄-alkyl,or R⁶, R⁷ furthermore together with the nitrogen atom to which they areattached represent an optionally C₁-C₂-alkyl-substituted five- orsix-membered cycle in which optionally one methylene group may bereplaced by oxygen.
 4. Compounds according to claim 1, characterized inthat K represents oxygen or sulphur, Ar represents Ar¹, where Ar¹represents phenyl which is optionally mono- to trisubstituted byfluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i-or t-butyl, methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy,allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy,methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy,methylenedioxy, difluoromethylenedioxy, tetra-fluoroethylenedioxy,difluoromethylthio, trifluoromethylthio, trifluoromethylsulphinyl,trifluoromethylsulphonyl, benzyloxy, hydroxyl, mercapto, nitro, cyano oramino, or represents pyridyl which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, propoxy,i-propoxy, butoxy, i-butoxy, methylthio, ethylthio or trifluoromethyl,or represents Ar², where Ar² represents Ar¹ which is additionallysubstituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl orphenoxy, where these substituents are for their part optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- ori-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- ort-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, orrepresents the group

 where B¹ represents hydrogen or fluorine and B⁸ represents allyl,propargyl or benzyl, X represents —CN, —CO—NH₂, or

Y represents hydrogen, in each case optionally mono- orpoly-hydroxy-substituted C₁-C₆-alkyl, C₁-C₄-halogenoalkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₄-alkoxy-C₂-C₃-alkyl,di-C₁-C₂-alkoxy-C₂-C₄-alkyl, C₁-C₂-alkoxy-C₂-C₄-cyanoalkyl,C₁-C₂-alkylthio-C₂-C₃-alkyl, C₁-C₅-halogenoalkenyl or C₁-C₆-cyanoalkyl,represents in each case optionally methyl-, methoxy-, ethoxy-,trifluoromethyl-, cyano-, chlorophenyl-, benzyl-, hydroxymethyl-,fluorine- or chlorine-substituted C₃-C₆-cycloalkyl orC₃-C₆-cycloalkyl-C₁-C₂-alkyl in which optionally one methylene group maybe replaced by oxygen or sulphur, represents benzyl, phenethyl orpyridylmethyl, each of which is optionallymono- to trisubstituted byfluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, cyano or nitro, Z representshydrogen, methyl, ethyl, represents phenyl or benzyl, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R³represents methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl,vinyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i-or t-butyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cyclopentyloxy,cyclohexyloxy, represents phenyl, pyridyl or benzyl, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine,methyl, n-, s-, i- or t-butyl, methoxy, trifluoromethyl,trifluoro-methoxy, cyano or nitro, or in the case of the radicals a), c)and f) mentioned under Ar, also represents the group

R⁵ represents hydrogen or methyl, R⁶ represents hydrogen, methyl, ethyl,propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl, cyclopentyl,cyclohexyl, represents phenyl which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, R⁷ represents hydrogen, methyl orethyl, or R⁶, R⁷ furthermore together with the nitrogen atom to whichthey are attached represent a pyrrolidine, piperidine or morpholineradical.
 5. Compounds according to claim 1, characterized in that Krepresents oxygen, Ar represents phenyl which is mono- orpolysubstituted by trifluoromethyl, fluorine, chlorine, allyloxy, cyano,benzyloxy, or represents the group

 where particular emphasis is given to the meanings4-chlorophenyl,3,5-di(trifluoromethyl)phenyl and 2-fluoro-4-chloro-5-allyloxy, Xrepresents CN, Y represents hydrogen, C₁-C₆-alkyl, C₁-C₃-halogenoalkyl,cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclopentylmethyl or cyclohexylmethyl, Z represents hydrogen or methyl.6. Process for preparing compounds according to any of claims 1 to 5,characterized in that (A) if K represents oxygen, compounds of theformula (II)

 in which Ar and X are each as defined in any of claims 1 to 5,  arereacted with compounds of the formula (III)

 in which Y and Z are each as defined in any of claims 1 to 5, but donot represent hydrogen, and W represents O or S(O)_(g), where grepresents 0 or 2, and R⁸ represents alkyl or benzyl,  if appropriate inthe presence of a diluent and if appropriate in the presence of a baseor a metal compound of the formula (IVa) Me(V)₂  (IVa)  in which Merepresents a divalent transition metal atom and V represents a chelateligand,  or that (B) if K represents oxygen, compounds of the formula(V)

 in which Ar and X are each as defined in any of claims 1 to 5, and Halrepresents halogen, are reacted with compounds of the formula (VI)

 in which Y and Z are each as defined in any of claims 1 to 5, but donot represent hydrogen,  if appropriate in the presence of a diluent togive compounds of the formula (VII)

 in which Ar, X, Y and Z are each as defined above,  which is reactedfurther, if appropriate in the presence of a base and if appropriate inthe presence of a trivalent phosphorus compound, with elimination ofsulphur and hydrogen halide, to give compounds of the formula (I) inwhich Ar, X, Y and Z are each as defined above,  or that (C) compoundsof the formula (II)

in which Ar and X are each as defined in any of claims 1 to 5,  areinitially condensed with compounds of the formula (VIII)

 in which Z is as defined above and R⁹ represents C₁-C₄-alkyl,  and theresulting intermediates are reacted with amines of the formula (IX)Y—NH₂  (IX)  in which Y is as defined in any of claims 1 to 5,  ifappropriate in the presence of a diluent and if appropriate in thepresence of a base,  or that (D) if K represents sulphur, compounds ofthe formula (I)

in which Ar, X, Y and Z are each as defined in any of claims 1 to 5 andK represents oxygen, are reacted in the presence of a sulphurizing agentsuch as, for example, phosphorus pentasulphide or2,4-bis-(4-methoxy)-1,2,3,4-dithiaphosphetane2,4-disulphide (Lawesson'sreagent) in the presence of a solvent,  or that (E) if Ar represents Ar²according to any of claims 1 to 5, compounds of the formula (I¹)

 in which Ar¹, X, Y and Z are each as defined in any of claims 1 to 5and Hal represents halogen,  are reacted with boronic acids of theformula (X) Ar^(2′)—B(OH)₂  (X),  in which Ar^(2′) represents thesubstituents which were mentioned in claim 1 as additional substituentsfor Ar¹  in the presence of a solvent, if appropriate in the presence ofa base and/or a noble metal complex.
 7. Herbicidal, acaricidal and/orinsecticidal compositions characterized in that they comprise at leastone compound according to any of claims 1 to 5 and customary extendersand/or surfactants.
 8. Use of compounds according to any of claims 1 to5 for controlling undesirable vegetation and/or animal pests.
 9. Methodfor controlling undesirable vegetation or animal pests, characterized inthat a compound according to any of claims 1 to 5 is allowed to act onundesirable plants or animal pests and/or their habitat.
 10. Process forpreparing herbicidal compositions, characterized in that a compoundaccording to any of claims 1 to 5 is mixed with customary extenders orsurfactants.